subject:(N heterocyclic carbene)

Colorado State University

1. Filloux, Claire M. Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity.

Degree: PhD, Chemistry, 2015, Colorado State University

URL: http://hdl.handle.net/10217/166906

► The chapters that follow describe two independent investigations. Both relay the development of experimental methods for the catalytic, asymmetric addition of carbon-hydrogen bonds to alkenes.… (more)

Subjects/Keywords: catalysis; organic; asymmetric; rhodium; N-heterocyclic carbene

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APA (6^th Edition):

Filloux, C. M. (2015). Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/166906

Chicago Manual of Style (16^th Edition):

Filloux, Claire M. “Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity.” 2015. Doctoral Dissertation, Colorado State University. Accessed April 18, 2021. http://hdl.handle.net/10217/166906.

MLA Handbook (7^th Edition):

Filloux, Claire M. “Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity.” 2015. Web. 18 Apr 2021.

Vancouver:

Filloux CM. Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity. [Internet] [Doctoral dissertation]. Colorado State University; 2015. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/10217/166906.

Council of Science Editors:

Filloux CM. Organocatalytic, Michael-Stetter reaction and rhodium(I)-catalyzed hydroheteroarylation of acrylates with benzoxazoles: reaction development and investigations into origins of enantioselectivity. [Doctoral Dissertation]. Colorado State University; 2015. Available from: http://hdl.handle.net/10217/166906

Australian National University

2. McQueen, Caitlin Meredith Anne. Unconventional pincer ligands and their transition metal complexes .

Degree: 2013, Australian National University

URL: http://hdl.handle.net/1885/11602

► This thesis describes investigations into unconventional pincer systems incorporating non-classical central donor groups. Direct reaction of 1,3-bis(diphenylphosphinomethyl)-2,3-dihydro-1H-1,3,2-benzodiazaborole (dppBH) with metal complexes and subsequent ligand manipulations… (more)

▼ This thesis describes investigations into unconventional pincer systems incorporating non-classical central donor groups. Direct reaction of 1,3-bis(diphenylphosphinomethyl)-2,3-dihydro-1H-1,3,2-benzodiazaborole (dppBH) with metal complexes and subsequent ligand manipulations have provided novel ruthenium and, for the first time, osmium boryl pincer complexes. The boryl complexes thus prepared have been observed to undergo various subsequent reactions involving the chloride and triphenylphosphine co-ligands to give new complexes. Further reactions of dppBH with complexes dichlorotris(triphenylphosphine)ruthenium(II) and -osmium(II) resulted in the first examples of sigma-borane pincer complexes, which represent intercepted intermediates in the B-H activation process, affording rare structural data for an osmium sigma-borane complex. The B-H bond of the ruthenium complex could be readily cleaved upon ligand manipulation, such as substitution of triphenylphosphine with the pi-acidic carbonyl and isocyanide ligands, which gave the disubstituted boryl complexes via spontaneous loss of HCl. Attempts to isolate a 1,8-diaminonaphthalene-based borane analogue of dppBH proved unsuccessful, though the compound 1,3 bis(diphenylphosphinomethyl)-2,3-dihydroperimidine (PhDHP) was obtained as a side-product in one case. Further investigations into this compound resulted in the development of a convenient one-pot synthesis, which could be extended to the cyclohexyl analogue 1,3 bis(dicyclohexylphosphinomethyl)-2,3-dihydroperimidine (CyDHP). These compounds were observed to react with various platinum group metal complexes to give novel N-heterocyclic carbene (NHC) pincer complexes via double geminal C-H activation of the central methylene group, providing the first examples of perimidine-based NHC inclusion as the central equatorial group of a pincer system. Reactions of dihydroperimidines with group 8 complexes dichlorotris(triphenylphosphine)ruthenium(II) and -osmium(II) have thus provided the novel pincer NHC complexes. However, reactions of PhDHP with dichlorotris(triphenylphosphine)ruthenium and CyDHP with less electron-rich ruthenium precursors instead gave asymmetric PNP coordinated complexes, in which C-H activation had not occurred, though this could be induced thermally in one case. Reactions of PhDHP and CyDHP with chlorotris(triphenylphosphine)rhodium(I) gave 16-electron chloro rhodium(I) NHC pincer complexes, and their reactivity was investigated via co-ligand manipulations and a preliminary catalytic study. The latter revealed that, while this complex was not particularly efficient for most of the reactions investigated, in some cases simple modifications of the co-ligands could substantially improve catalytic activity. Reactions of the pro-ligands with iridium precursors instead favoured the formation of coordinatively saturated complexes. The reaction of CyDHP with chlorobis(cyclooctene)iridium(I) dimer resulted in a dihydrido chloro iridium(III) NHC pincer complex, while reaction with…

Subjects/Keywords: organometallic; chemistry; pincer; N-heterocyclic carbene; boryl

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APA (6^th Edition):

McQueen, C. M. A. (2013). Unconventional pincer ligands and their transition metal complexes . (Thesis). Australian National University. Retrieved from http://hdl.handle.net/1885/11602

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

McQueen, Caitlin Meredith Anne. “Unconventional pincer ligands and their transition metal complexes .” 2013. Thesis, Australian National University. Accessed April 18, 2021. http://hdl.handle.net/1885/11602.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

McQueen, Caitlin Meredith Anne. “Unconventional pincer ligands and their transition metal complexes .” 2013. Web. 18 Apr 2021.

Vancouver:

McQueen CMA. Unconventional pincer ligands and their transition metal complexes . [Internet] [Thesis]. Australian National University; 2013. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/1885/11602.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

McQueen CMA. Unconventional pincer ligands and their transition metal complexes . [Thesis]. Australian National University; 2013. Available from: http://hdl.handle.net/1885/11602

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Tasmania

3. Wierenga, TS. N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles.

Degree: 2019, University of Tasmania

URL: https://eprints.utas.edu.au/31480/1/Wierenga_whole_thesis.pdf ; Wierenga, TS ORCID: 0000-0002-0752-6561 <https://orcid.org/0000-0002-0752-6561> 2019 , 'N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles', PhD thesis, University of Tasmania.

► α-Cyanocarbanion complexes are an interesting class of complexes that contain a nitrile ligand featuring a deprotonated α-carbon. Chapter 1 gives an overview of the various… (more)

Subjects/Keywords: N-heterocyclic carbene; Palladium; Nickel; catalysis; alkylnitriles

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APA (6^th Edition):

Wierenga, T. (2019). N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles. (Thesis). University of Tasmania. Retrieved from https://eprints.utas.edu.au/31480/1/Wierenga_whole_thesis.pdf ; Wierenga, TS ORCID: 0000-0002-0752-6561 <https://orcid.org/0000-0002-0752-6561> 2019 , 'N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles', PhD thesis, University of Tasmania.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Wierenga, TS. “N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles.” 2019. Thesis, University of Tasmania. Accessed April 18, 2021. https://eprints.utas.edu.au/31480/1/Wierenga_whole_thesis.pdf ; Wierenga, TS ORCID: 0000-0002-0752-6561 <https://orcid.org/0000-0002-0752-6561> 2019 , 'N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles', PhD thesis, University of Tasmania..

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Wierenga, TS. “N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles.” 2019. Web. 18 Apr 2021.

Vancouver:

Wierenga T. N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles. [Internet] [Thesis]. University of Tasmania; 2019. [cited 2021 Apr 18]. Available from: https://eprints.utas.edu.au/31480/1/Wierenga_whole_thesis.pdf ; Wierenga, TS ORCID: 0000-0002-0752-6561 <https://orcid.org/0000-0002-0752-6561> 2019 , 'N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles', PhD thesis, University of Tasmania..

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Wierenga T. N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles. [Thesis]. University of Tasmania; 2019. Available from: https://eprints.utas.edu.au/31480/1/Wierenga_whole_thesis.pdf ; Wierenga, TS ORCID: 0000-0002-0752-6561 <https://orcid.org/0000-0002-0752-6561> 2019 , 'N-heterocyclic carbene-based Pd and Ni complexes and their applications to the activation of alkylnitriles', PhD thesis, University of Tasmania.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Edinburgh

4. Marr, Isobel Helen. Synthesis and reactivity of scandium N-heterocyclic carbene complexes.

Degree: PhD, 2014, University of Edinburgh

URL: http://hdl.handle.net/1842/17970

► Chapter one introduces N-heterocyclic carbenes (NHCs) and discusses their use as ligands for rare earth metal complexes, with particular emphasis upon compounds synthesised from 2009… (more)

▼ Chapter one introduces N-heterocyclic carbenes (NHCs) and discusses their use as ligands for rare earth metal complexes, with particular emphasis upon compounds synthesised from 2009 until the present day. Chapter two details the synthesis and characterisation of the homoleptic scandium-NHC complex [Sc(L)3] (L = [OCMe2CH2(1-C{NCHCHNiPr})]). Reactions of [Sc(L)3] with boranes, CO2 and CS2 are described which exploit the relative lability of the Sc–Ccarbene bond and allow formation of [Sc(L)2(OCMe2CH2(1-B'C{NCHCHNiPr}))] (B' = 9-BBN, BPh3, B(C6F5)3, BH3), [Sc(OCMe2CH2(1-O2CC{NCHCHNiPr})3]n, [Sc(L)2(OCMe2CH2 (1-S2CC{NCHCHNiPr})] and [Sc(L)(OCMe2CH2(1-S2CC{NCHCHNiPr})2]2. The chapter also discusses the reactivity of [Sc(L)3] towards substrates containing acidic C–H and N–H bonds and substrates containing polar E–X bonds (where E = C, Si, B, P and X = Cl, I). Chapter three describes the synthesis and characterisation of the NHC substituted scandium benzyl complexes [Sc(Bn)2(L)]2 and [Sc(Bn)(L)2], and the attempted synthesis of NHC substituted scandium aminobenzyl complexes. The reactivity of [Sc(Bn)2(L)]2 with RX substrates (R = alkyl) is discussed in detail; depending on the nature of the alkyl group, these reactions can allow formation of R–Bn , the result of carbon-carbon coupling. The complex [Sc(Bn)(L)Cl]2 has been isolated from these reactions and is structurally characterised. The reactivity of [Sc(Bn)2(L)]2 towards C–H bonds is explored and attempts to prepare NHC substituted scandium hydrides are described. Comparisons of the relative stability and reactivity of [Sc(Bn)2(L)]2 and [Sc(Bn)3(thf)3] are drawn. Chapter four documents the synthesis and characterisation of [Sc(Odtbp)2(L)] (Odtbp = 2,6-di-tert-butylphenoxide), [Sc(Odtbp)(L)2], and the samarium analogue [Sm(Odtbp)(L)2]. The reactivity of these complexes towards various small molecules is described. The chapter also details attempts to prepare the cationic scandium complexes [Sc(L)2][Bort] (Bort = bis[3,3',5,5'-tetra-(tert-butyl)-2,2-diphenolato]borate) and [Sc(L)2][B(Ph)4]. Chapter five provides overall conclusions to the work presented in this thesis. Chapter six contains all experimental and characterising data for the complexes and reactions detailed in this work.

Subjects/Keywords: 547; scandium; N-heterocyclic carbene; NHC

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APA (6^th Edition):

Marr, I. H. (2014). Synthesis and reactivity of scandium N-heterocyclic carbene complexes. (Doctoral Dissertation). University of Edinburgh. Retrieved from http://hdl.handle.net/1842/17970

Chicago Manual of Style (16^th Edition):

Marr, Isobel Helen. “Synthesis and reactivity of scandium N-heterocyclic carbene complexes.” 2014. Doctoral Dissertation, University of Edinburgh. Accessed April 18, 2021. http://hdl.handle.net/1842/17970.

MLA Handbook (7^th Edition):

Marr, Isobel Helen. “Synthesis and reactivity of scandium N-heterocyclic carbene complexes.” 2014. Web. 18 Apr 2021.

Vancouver:

Marr IH. Synthesis and reactivity of scandium N-heterocyclic carbene complexes. [Internet] [Doctoral dissertation]. University of Edinburgh; 2014. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/1842/17970.

Council of Science Editors:

Marr IH. Synthesis and reactivity of scandium N-heterocyclic carbene complexes. [Doctoral Dissertation]. University of Edinburgh; 2014. Available from: http://hdl.handle.net/1842/17970

University of Texas – Austin

5. Wang, Weiran. Toward the synthesis of a catalytic conducting metallopolymer for cross-coupling reactions.

Degree: MA, Chemistry, 2017, University of Texas – Austin

URL: http://hdl.handle.net/2152/72467

► The thiophene-based metallopolymer provides a great template for redox-active catalysts. Chemical or electrochemical doping of the metallopolymer can generate charged species within the polymer backbone… (more)

Subjects/Keywords: Metallopolymer; N-heterocyclic carbene; Redox-active ligand

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APA (6^th Edition):

Wang, W. (2017). Toward the synthesis of a catalytic conducting metallopolymer for cross-coupling reactions. (Masters Thesis). University of Texas – Austin. Retrieved from http://hdl.handle.net/2152/72467

Chicago Manual of Style (16^th Edition):

Wang, Weiran. “Toward the synthesis of a catalytic conducting metallopolymer for cross-coupling reactions.” 2017. Masters Thesis, University of Texas – Austin. Accessed April 18, 2021. http://hdl.handle.net/2152/72467.

MLA Handbook (7^th Edition):

Wang, Weiran. “Toward the synthesis of a catalytic conducting metallopolymer for cross-coupling reactions.” 2017. Web. 18 Apr 2021.

Vancouver:

Wang W. Toward the synthesis of a catalytic conducting metallopolymer for cross-coupling reactions. [Internet] [Masters thesis]. University of Texas – Austin; 2017. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/2152/72467.

Council of Science Editors:

Wang W. Toward the synthesis of a catalytic conducting metallopolymer for cross-coupling reactions. [Masters Thesis]. University of Texas – Austin; 2017. Available from: http://hdl.handle.net/2152/72467

University of Akron

6. Wright, Brian D. Synthesis, Characterization, and Biological Activity of Silver Carbene Complexes and Their Precursors.

Degree: PhD, Chemistry, 2012, University of Akron

URL: http://rave.ohiolink.edu/etdc/view?acc_num=akron1353423024

► Since the discovery of the first stable silver N-heterocyclic carbene complex by Arduengo in 1991, the field of silver N-heterocyclic carbene complexes has expanded… (more)

▼ Since the discovery of the first stable silver N-heterocyclic carbene complex by Arduengo in 1991, the field of silver N-heterocyclic carbene complexes has expanded greatly. These complexes have been studied extensively for use in catalysis, as transmetallation agents, and more recently for pharmaceutical applications. Silver has been used for centuries as an anti-microbial agent, and more recently has been shown to have anti-tumor activity as well. Combination with the easily modified N-heterocyclic carbene ligand yields a drug that can be rationally designed for increased water solubility, increased lipophilicity, or to increase activity. These complexes have shown great results, and will be the main focus of this dissertation. Chapter 1 of this dissertation reviews silver N-heterocyclic carbene complexes as promising antimicrobial agents and the evolution of the field over the past two decades. Chapter 2 discusses the synthesis of a new N-heterocyclic carbene backbone, 4,5,6,7-tetrachlorobenzimidazole, and the corresponding silver complexes for antimicrobial use. These complexes were then examined in vitro against a panel of clinical bacteria, displaying inhibitory concentrations between 0.25-4 µg/mL. Additionally, two of the silver complexes displayed antimicrobial activity against a silver-resistant E. coli strain. Chapter 3 discusses the rational design of several new naphthalene containing imidazolium cations, the precursors to silver N-heterocyclic carbene complexes, for the use as anti-tumor drugs. These new imidazolium cations have been designed to increase water solubility, anti-tumor activity, and encapsulation efficiency into biodegradable delivery devices through modification of the substituents. These cations have demonstrated in vitro anti-tumor activity comparable to cisplatin against three types of lung cancer. The anti-tumor activity increased with the increase in the length of the alkyl chain substituent. Additionally, it was noted that the position of the alkyl chain on the naphthalene rings did not affect the anti-tumor activity of the cations. Chapter 4 discusses the in vitro anti-tumor activity of silver carbene complexes based on selected imidazolium cations from chapter 3. These complexes have demonstrated an increase in water solubility in comparison to previously reported silver N-heterocyclic carbene anti-tumor complexes. Additionally, the complexes have displayed anti-tumor activity at clinically relevant levels, demonstrating IC50 values ranging from 5-25 µg/mL. In general, the anti-tumor activity increased as the length of the alkyl chain on the ligand increased. The highest activity was displayed by SCC44, which unlike the other complexes contained two naphthalene rings. Advisors/Committee Members: Youngs, Wiley (Advisor).

Subjects/Keywords: Chemistry; Antimicrobial; Anticancer; Anti-tumor; Silver; NHC; N-heterocyclic Carbene; Carbene

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APA (6^th Edition):

Wright, B. D. (2012). Synthesis, Characterization, and Biological Activity of Silver Carbene Complexes and Their Precursors. (Doctoral Dissertation). University of Akron. Retrieved from http://rave.ohiolink.edu/etdc/view?acc_num=akron1353423024

Chicago Manual of Style (16^th Edition):

Wright, Brian D. “Synthesis, Characterization, and Biological Activity of Silver Carbene Complexes and Their Precursors.” 2012. Doctoral Dissertation, University of Akron. Accessed April 18, 2021. http://rave.ohiolink.edu/etdc/view?acc_num=akron1353423024.

MLA Handbook (7^th Edition):

Wright, Brian D. “Synthesis, Characterization, and Biological Activity of Silver Carbene Complexes and Their Precursors.” 2012. Web. 18 Apr 2021.

Vancouver:

Wright BD. Synthesis, Characterization, and Biological Activity of Silver Carbene Complexes and Their Precursors. [Internet] [Doctoral dissertation]. University of Akron; 2012. [cited 2021 Apr 18]. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=akron1353423024.

Council of Science Editors:

Wright BD. Synthesis, Characterization, and Biological Activity of Silver Carbene Complexes and Their Precursors. [Doctoral Dissertation]. University of Akron; 2012. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=akron1353423024

7. Hippolyte, Laura. New syntheses of N-heterocyclic carbene-stabilized gold nanoparticles : Nouvelles synthèses de nanoparticules d'or stabilisées par des carbènes N-hétérocycliques.

Degree: Docteur es, Chimie des matériaux, 2018, Sorbonne université

URL: http://www.theses.fr/2018SORUS148

►

Récemment, les carbènes N-hétérocycliques (NHC) ont suscité un intérêt important dans le domaine de la chimie des matériaux. En effet, cette nouvelle catégorie de ligands… (more)

▼

Récemment, les carbènes N-hétérocycliques (NHC) ont suscité un intérêt important dans le domaine de la chimie des matériaux. En effet, cette nouvelle catégorie de ligands forme des liaisons très fortes avec une diversité de métaux et leur structure, ainsi que leurs propriétés électroniques, peuvent être adaptées par de la synthèse organique. Cette forte liaison est d’un intérêt particulier dans le domaine des nanoparticules d’or (NP) et des synthèses ont déjà été proposées. En effet, les NPs présentent de nombreuses applications potentielles, par exemple dans les capteurs, en catalyse ou médecine, mais ces applications sont parfois freinées par un manque de stabilité du ligand de surface. Ce travail de thèse s’est concentré sur le développement de nouvelles synthèses de nanoparticules d’or stabilisées par des NHC. D’abord, en revisitant une procédure existante à base de sels d’imidazoliums, ce qui a mené à une synthèse n’utilisant que les composés commerciaux : AuCl et NaBH4 et des halogénures d’imidazolium, facilement obtenus. Une synthèse totalement nouvelle a ensuite été développée en utilisant des NHC-boranes qui sont des adduits de Lewis stables. Nous avons montré pour la première fois que les NHC-boranes peuvent être utilisés comme réactifs "2-en-1" dans la synthèse de NP : comme réducteurs du précurseur d’or et comme source de NHC. Enfin, nous sommes les premiers à décrire la synthèse de NP stabilisées par des carbènes mésoioniques (MIC).Les MICs sont une sous-catégorie des NHCs qui sont préparés par « chimie click » et qui présentent des propriétés électroniques uniques. Un intérêt particulier a été porté à la caractérisation des nanoparticules, notamment par XPS.

Over the past decade, N-heterocyclic carbenes (NHC) have drawn considerable interest in the field of materials chemistry. Indeed, this relatively new class of ligands forms strong bonds with a wide range of metals and their structures and electronic properties can be tuned “at-will” through organic synthesis. This strong bond is of particular interest for gold nanoparticles. Indeed, gold nanoparticles have many potential applications, for example in sensors, catalysis or medicine, but those potential applications are sometimes hindered by a lack of stability of the surface ligand. A few syntheses of NHC-stabilized gold nanoparticles have already been described in the literature but each presents their own set of drawbacks. This thesis work has focused on the development of new syntheses of NHC-stabilized gold nanoparticles. First, by revisiting a literature procedure starting from imidazolium salts, we managed to develop a one-pot synthesis starting only from commercially available AuCl, NaBH4 and easily synthesized imidazolium salts. A totally new synthesis was developed using NHC-boranes, which are stable Lewis adducts. Here, we reported for the first time their use as a 2-in-1 reagent, able to reduce the metallic precursor and provide the nanoparticles stabilizing ligands. Finally, we are the first to report a synthesis of gold nanoparticles…

Advisors/Committee Members: Ribot, François (thesis director), Fensterbank, Louis (thesis director).

Subjects/Keywords: Nanoparticules; Or; Carbène N-Hétérocyclique; Carbène N-Hétérocyclique borane; Carbene mésoionique; Spectrométrie photoélectronique X; Nanoparticles; Gold; N-Heterocyclic Carbene; Carbene N-Heterocyclic borane; Mesoionic carbenes; X-ray photoelectron spectrometry; 541.042

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APA (6^th Edition):

Hippolyte, L. (2018). New syntheses of N-heterocyclic carbene-stabilized gold nanoparticles : Nouvelles synthèses de nanoparticules d'or stabilisées par des carbènes N-hétérocycliques. (Doctoral Dissertation). Sorbonne université. Retrieved from http://www.theses.fr/2018SORUS148

Chicago Manual of Style (16^th Edition):

Hippolyte, Laura. “New syntheses of N-heterocyclic carbene-stabilized gold nanoparticles : Nouvelles synthèses de nanoparticules d'or stabilisées par des carbènes N-hétérocycliques.” 2018. Doctoral Dissertation, Sorbonne université. Accessed April 18, 2021. http://www.theses.fr/2018SORUS148.

MLA Handbook (7^th Edition):

Hippolyte, Laura. “New syntheses of N-heterocyclic carbene-stabilized gold nanoparticles : Nouvelles synthèses de nanoparticules d'or stabilisées par des carbènes N-hétérocycliques.” 2018. Web. 18 Apr 2021.

Vancouver:

Hippolyte L. New syntheses of N-heterocyclic carbene-stabilized gold nanoparticles : Nouvelles synthèses de nanoparticules d'or stabilisées par des carbènes N-hétérocycliques. [Internet] [Doctoral dissertation]. Sorbonne université; 2018. [cited 2021 Apr 18]. Available from: http://www.theses.fr/2018SORUS148.

Council of Science Editors:

Hippolyte L. New syntheses of N-heterocyclic carbene-stabilized gold nanoparticles : Nouvelles synthèses de nanoparticules d'or stabilisées par des carbènes N-hétérocycliques. [Doctoral Dissertation]. Sorbonne université; 2018. Available from: http://www.theses.fr/2018SORUS148

University of Edinburgh

8. Germeroth, Anne Inger. Reactivity of electropositive f-block metal N-heterocyclic carbene complexes.

Degree: PhD, 2013, University of Edinburgh

URL: http://hdl.handle.net/1842/9519

► The combination of Lewis acidic f-block metals and a labile nucleophilic carbene can be an excellent means to activate small molecules such as silanes, CO2… (more)

▼ The combination of Lewis acidic f-block metals and a labile nucleophilic carbene can be an excellent means to activate small molecules such as silanes, CO2 and other traditionally inert substrates. Furthermore, bidentate alkoxy-NHC ligands have shown promise in the support of unusual high oxidation state organometallic complexes, including examples of CeIV, PdIV and UVI. In this thesis the synthesis and reactivity of a series of f-block metal NHC complexes is described. Chapter One introduces N-heterocyclic carbenes and their f-block metal complexes, in particular of cerium, praseodymium and uranium. Furthermore, it will give an overview of small molecule activation by NHCs, lanthanides and specifically [Ce(LAr)N"], (L = OC(CH3)2CH2(CNCH2CH2NMes) the magnetic properties and use of lanthanides e.g. as single molecule magnets and oxo-functionalisation of the uranyl moiety. Chapter Two describes the addition-elimination reaction chemistry of CeIII and UIV NHC complexes in which polar reagents add in a heterocyclic fashion across the MNHC bond. It also describes the synthesis of the lithium salt of the alkoxycarbene proligand [LiLAr]4 and its reactivity towards f-element halide and aryloxide salts. A series of reactions to target the formation of metal-metal bonds is described. Chapter Three focuses on the synthesis of novel cerium and praseodymium complexes [Pr(LAr)N"2], [Pr(LAr)2N"], [Pr(OAr2,6-tBu)3] and [Ce(OAr2,6-tBu)3] and their reactivity towards oxidants. A series of alkoxide bridged lanthanide dimers [(Cl)Ce(μ- LAr)2Ce(Cl)2], [N"(LAr)Ce(μ-OAr2,6-tBu)OAr2,6- 2Ce(LAr)N"] and [N"(Cl)Pr(μ LAr)2Pr(Cl)N"] have been made and characterised including by SQUID variable temperature magnetometry. Chapter Four evaluates the synthesis and reactivity of uranyl complexes [UO2(LAr)2], [UO2N"2(py)2] and [UO2(OAr2,6-tBu)2(py)2], specifically their reactivity towards haloboranes in different solvents. Additionally, the oxo-functionalisation of uranyl compounds with haloboranes is discussed. Chapter Five draws conclusions and provides a summary of the work presented. Chapter Six comprises the experimental details and analytical data.

Subjects/Keywords: 546; inorganic chemistry; organometallic; f-element; carbene; N-heterocyclic carbene; uranyl; synthesis; ligand

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APA (6^th Edition):

Germeroth, A. I. (2013). Reactivity of electropositive f-block metal N-heterocyclic carbene complexes. (Doctoral Dissertation). University of Edinburgh. Retrieved from http://hdl.handle.net/1842/9519

Chicago Manual of Style (16^th Edition):

Germeroth, Anne Inger. “Reactivity of electropositive f-block metal N-heterocyclic carbene complexes.” 2013. Doctoral Dissertation, University of Edinburgh. Accessed April 18, 2021. http://hdl.handle.net/1842/9519.

MLA Handbook (7^th Edition):

Germeroth, Anne Inger. “Reactivity of electropositive f-block metal N-heterocyclic carbene complexes.” 2013. Web. 18 Apr 2021.

Vancouver:

Germeroth AI. Reactivity of electropositive f-block metal N-heterocyclic carbene complexes. [Internet] [Doctoral dissertation]. University of Edinburgh; 2013. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/1842/9519.

Council of Science Editors:

Germeroth AI. Reactivity of electropositive f-block metal N-heterocyclic carbene complexes. [Doctoral Dissertation]. University of Edinburgh; 2013. Available from: http://hdl.handle.net/1842/9519

University of Alberta

9. Powers, Katherine. N-Heterocyclic Olefins: An Investigation into a Developing Class of Ligands.

Degree: MS, Department of Chemistry, 2016, University of Alberta

URL: https://era.library.ualberta.ca/files/c8c97kq48p

► An investigation into the relatively new carbene class, N-heterocyclic olefins (NHOs) was completed. An improved synthesis of the ligand was developed. NHOs were tested as… (more)

Subjects/Keywords: N-heterocyclic olefins; bonding; transition metal; catalysis; carbene

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APA (6^th Edition):

Powers, K. (2016). N-Heterocyclic Olefins: An Investigation into a Developing Class of Ligands. (Masters Thesis). University of Alberta. Retrieved from https://era.library.ualberta.ca/files/c8c97kq48p

Chicago Manual of Style (16^th Edition):

Powers, Katherine. “N-Heterocyclic Olefins: An Investigation into a Developing Class of Ligands.” 2016. Masters Thesis, University of Alberta. Accessed April 18, 2021. https://era.library.ualberta.ca/files/c8c97kq48p.

MLA Handbook (7^th Edition):

Powers, Katherine. “N-Heterocyclic Olefins: An Investigation into a Developing Class of Ligands.” 2016. Web. 18 Apr 2021.

Vancouver:

Powers K. N-Heterocyclic Olefins: An Investigation into a Developing Class of Ligands. [Internet] [Masters thesis]. University of Alberta; 2016. [cited 2021 Apr 18]. Available from: https://era.library.ualberta.ca/files/c8c97kq48p.

Council of Science Editors:

Powers K. N-Heterocyclic Olefins: An Investigation into a Developing Class of Ligands. [Masters Thesis]. University of Alberta; 2016. Available from: https://era.library.ualberta.ca/files/c8c97kq48p

Stellenbosch University

10. Ngodwana, Lonwabo. Resorcin[4]arene based N-heterocyclic carbenes as catalysts for carbon-carbon formation.

Degree: PhD, 2016, Stellenbosch University

URL: http://hdl.handle.net/10019.1/100377

►

ENGLISH ABSTRACT: Resorcin[4]arenes are 3-dimensional cyclic tetramers belonging to a class of compounds called cyclophanes. Because of their properties, including several sites of functionalization and… (more)

▼

ENGLISH ABSTRACT: Resorcin[4]arenes are 3-dimensional cyclic tetramers belonging to a class of compounds called cyclophanes. Because of their properties, including several sites of functionalization and possession of a cavity, these compounds found their way into several applications. These include cation extraction, ion exchange mimics, molecular switches and catalysis. The latter is still at its infancy. This work was aimed at developing the first examples of resorcin[4]arene based Nheterocyclic carbene (NHC) complexes of palladium and evaluating their potential for catalysis of carbon-carbon bond formatting reactions. Using an ortholithiation technology that was developed in our group, a distally functionalized resorcin[4]arene di-ester was prepared. The reduction of the ester and bromination of the resulting di-ol led to a distal bromomethylresorcin[4]arene. The reactions of this new resorcin[4]arene with a variety of N-alkylimidazoles gave a small library of resorcin[4]arene imidazolium NHC precursor salts. Initially, the preparation of a bidentate palladium complex from the salts was attempted. The metal complex was isolated in 35% yield from an N-mesityl imidazolium salt. When the preparation of a dinuclear metal complex series, i.e. PEPPSI, was attempted, the compounds in this class could be isolated in yields over 90%. Although these compounds show the expected coordination modes (square-planer Pd center), they showed some variations in solid state conformations. Resorcin[4]arene NHC compounds, both pre-formed and prepared in situ, were evaluated for catalytic ability in the Suzuki-Miyauri and Tsuji-Trost reactions. These compounds could facilitate moderate to complete conversion of starting materials to products.

AFRIKAANSE OPSOMMING: Resorsin[4]arene is 3-demensionele sikliese tertramere wat behoort aan ‘n klas verbindings genaamd siklofage. As gevolg van hulle eienskappe, onder andere ‘n menigte hoeveelheid funksionele groepe as ook ‘n molekulêre holte, het hierdie klas verbindings verskeie toepassings. Van hierdie toepassings sluit in katioon ekstraksie, ioonuitruiling nabootsing, molekulêre aanskakelaars en kataliese. Die laasgenoemde punt is nogsteeds in die vroeë stadium van navorsing. Die werk beoog om die eerste voorbeelde van resorsin[4]areen gebaseerde Nheterosikliese karbeen (NHK) komplekse met palladium te ontwikkel, gevolg deur die komplekse se potensiaal vir koolstof-koolstof bindingsvorming reaksies te evalueer. Deur die gebruik van orto-litiëring tegnologie wat ontwikkel is in ons groep is ‘n distaal gefunksioniseerde resorsin[4]areen di-ester gesintetiseer. Na die reduksie van die ester en gevolglike bromering van die diol was n distaal bromometielresorsin[4]arene geskep. Reaksies met hierdie nuwe resorsin[4]areen met ‘n verskeidenheid N-alkielimidasole het ‘n klein versameling van resorsin[4]areen imidasolium NHK voorloper soute gelewer. Aanvanklik was die poging om ‘n bidentate palladium kompleks van hierdie soute te sintetiseer. Die gebruik van ‘n sekere…

Advisors/Committee Members: Arnott, Gareth, Van Otterlo, Willem, Stellenbosch University. Faculty of Science. Chemistry and Polymer Science..

Subjects/Keywords: Resorcin[4]arene; Carbenes (Methylene compounds); N-heterocyclic carbene; Catalysis; UCTD

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APA (6^th Edition):

Ngodwana, L. (2016). Resorcin[4]arene based N-heterocyclic carbenes as catalysts for carbon-carbon formation. (Doctoral Dissertation). Stellenbosch University. Retrieved from http://hdl.handle.net/10019.1/100377

Chicago Manual of Style (16^th Edition):

Ngodwana, Lonwabo. “Resorcin[4]arene based N-heterocyclic carbenes as catalysts for carbon-carbon formation.” 2016. Doctoral Dissertation, Stellenbosch University. Accessed April 18, 2021. http://hdl.handle.net/10019.1/100377.

MLA Handbook (7^th Edition):

Ngodwana, Lonwabo. “Resorcin[4]arene based N-heterocyclic carbenes as catalysts for carbon-carbon formation.” 2016. Web. 18 Apr 2021.

Vancouver:

Ngodwana L. Resorcin[4]arene based N-heterocyclic carbenes as catalysts for carbon-carbon formation. [Internet] [Doctoral dissertation]. Stellenbosch University; 2016. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/10019.1/100377.

Council of Science Editors:

Ngodwana L. Resorcin[4]arene based N-heterocyclic carbenes as catalysts for carbon-carbon formation. [Doctoral Dissertation]. Stellenbosch University; 2016. Available from: http://hdl.handle.net/10019.1/100377

Texas A&M University

11. Pulukkody, Randara. Synthetic Analogues of Dinitrosyl Iron Complexes: Reactivity Studies and Improvements towards Therapeutic Applications.

Degree: PhD, Chemistry, 2015, Texas A&M University

URL: http://hdl.handle.net/1969.1/155488

► Dinitrosyl iron complexes (DNICs) are organometallic-like compounds formed endogenously as products of degradation of iron-sulfur clusters by NO or its interaction with the cellular chelatable… (more)

▼ Dinitrosyl iron complexes (DNICs) are organometallic-like compounds formed endogenously as products of degradation of iron-sulfur clusters by NO or its interaction with the cellular chelatable iron pool. Substantial evidence has accrued on the role of DNICs as endogenous transport and storage agents for the highly reactive NO radical. Such biological significance has led to biomimetic work on such entities in synthetic inorganic chemistry. Recently, such synthetic models have emerged as a new class of potential NO releasing agents. A series of N-heterocyclic carbene (NHC)-stabilized oxidized and reduced DNICs ({Fe(NO)2}⁹ /{Fe(NO)2}¹⁰: Enemark-Feltham notation) appeared promising candidates for further investigations on the reactivity of DNICs and on synthetic improvements for possible therapeutic applications. Planar NHC ligands mimic ligands such as imidazole, itself a surrogate for histidine. A base-promoted conversion was observed of an N-alkyl imidazole bearing, neutral {Fe(NO)2}¹⁰ DNIC to the NHC-DNIC, while maintaining the Fe(NO)2 unit intact. Subsequent alkylation led to the isolation of the NHC-DNIC product; signifying the integrity of the Fe(NO)² unit and further establishing that NHCs are ‘better’ ligands to Fe(NO)2 than imidazoles. Making use of an NHC-stabilized DNIC [(NHC)(RS)Fe(NO)2], a RS^−/RS• oxidation process in the presence of added CO was discovered, wherein the oxidized {Fe(NO)2}⁹ is reduced to {Fe(NO)2}¹⁰ through carbon monoxide (CO)/RS• ligand substitution. Kinetic studies established a bimolecular rate law and activation parameters suggested an associative mechanism. Computational results indicated a unique role for the delocalized frontier molecular orbitals of the Fe(NO)2 unit, involving an initial side-on approach of CO to the electron-rich N-Fe-N site. Attempts to further test the aforementioned computational proposal employed classical Hammett correlations for the elucidation of structure-activity relationships. Hammett correlations were used to monitor the changes in electron density at the {Fe(NO)2} unit and effects on the rate of reaction with CO of a series of (NHC)(SPhX)Fe(NO)2 derivatives with varying para substituents at the aryl thiolate. In accordance with the computational mechanistic proposal, rate enhancement was observed with increasing electron donating ability of the substituents. Although DNICs appear to be promising candidates in the context of nitric oxide releasing therapeutics, their lack of biocompatibility has hindered the progress of such applicability. The first examples of ‘sugar appended’ monomeric and dimeric DNICs were synthesized, making use of the tuning sites provided by the NHC-DNIC architecture. Such efforts are among the few examples for the synthesis of bio-functionalized DNICs. Advisors/Committee Members: Darensbourg, Marcetta Y (advisor), Gabbaï, François P (committee member), Barondeau, David P (committee member), Reinhart, Gregory D (committee member).

Subjects/Keywords: Dinitrosyl iron complexes; N-heterocyclic carbene; carbon monoxide

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APA (6^th Edition):

Pulukkody, R. (2015). Synthetic Analogues of Dinitrosyl Iron Complexes: Reactivity Studies and Improvements towards Therapeutic Applications. (Doctoral Dissertation). Texas A&M University. Retrieved from http://hdl.handle.net/1969.1/155488

Chicago Manual of Style (16^th Edition):

Pulukkody, Randara. “Synthetic Analogues of Dinitrosyl Iron Complexes: Reactivity Studies and Improvements towards Therapeutic Applications.” 2015. Doctoral Dissertation, Texas A&M University. Accessed April 18, 2021. http://hdl.handle.net/1969.1/155488.

MLA Handbook (7^th Edition):

Pulukkody, Randara. “Synthetic Analogues of Dinitrosyl Iron Complexes: Reactivity Studies and Improvements towards Therapeutic Applications.” 2015. Web. 18 Apr 2021.

Vancouver:

Pulukkody R. Synthetic Analogues of Dinitrosyl Iron Complexes: Reactivity Studies and Improvements towards Therapeutic Applications. [Internet] [Doctoral dissertation]. Texas A&M University; 2015. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/1969.1/155488.

Council of Science Editors:

Pulukkody R. Synthetic Analogues of Dinitrosyl Iron Complexes: Reactivity Studies and Improvements towards Therapeutic Applications. [Doctoral Dissertation]. Texas A&M University; 2015. Available from: http://hdl.handle.net/1969.1/155488

University of Delaware

12. Cobb, Kelsey M. Stereospecific, nickel-catalyzed cross-couplings of amine and alcohol derived substrates.

Degree: PhD, University of Delaware, Department of Chemistry and Biochemistry, 2017, University of Delaware

URL: http://udspace.udel.edu/handle/19716/21815

► This dissertation focuses on nickel-catalyzed cross-couplings of amine and alcohol derivatives to set stereogenic centers. Chapter 1 focuses on the cross-coupling of benzylic ammonium triflates… (more)

▼ This dissertation focuses on nickel-catalyzed cross-couplings of amine and alcohol derivatives to set stereogenic centers. Chapter 1 focuses on the cross-coupling of benzylic ammonium triflates with aryl, heteroaryl, and vinyl boronic acids. This method expands the scope of previous methods from our group, utilizing Ni(cod)2 without any additional phosphine or N-heterocyclic carbene (NHC) ligands. This reaction allows for cross-coupling of both naphthyl and phenyl substituted ammonium salts. The mild conditions of this reaction displays excellent functional group tolerance. ☐ Chapter 2 focuses on the cross-coupling of benzylic ammonium triflates with bis(pinacolato)diboron to afford secondary benzylic boronates with excellent chirality transfer, This reaction utilizes Ni(cod)2 as a catalyst with either phosphine or NHC ligands. The reaction proceeds with mild reaction conditions and excellent functional group tolerance. It allows for the cross-coupling of both naphthyl and phenyl substituted ammonium salts. This is the first example of a Miyaura borylation of a non-allylic electrophile to deliver products in highly enantioenriched form. ☐ Chapter 3 describes the development of the cross-coupling of tertiary benzylic acetates to form all-carbon quaternary stereocenters. This reaction prioritizes the use of an air-stable nickel(II) catalyst and environmentally friendly 2-Me-THF. The mild reaction conditions allow for excellent functional group tolerance. The reaction provides an efficient route to both di-aryl and tri-aryl quaternary stereocenters in high stereochemical fidelity. This method shows an expansion in transition metal catalysis to go beyond electrophiles adjacent to functional groups such as carbonyls and alkenes, and displays the possibility for tertiary benzylic electrophiles to under go transition metal catalysis. ☐ Chapter 4 focuses on the cross-coupling of enantioenriched allylic pivalates with aryl and heteroaryl borxines to form allylic, all-carbon quaternary stereocenters. This utilizes an air-stable nickel (II) catalyst, and functional group tolerant boroxine coupling partners to afford these quaternary stereocenters with high stereochemical fidelity. This reaction provides a powerful way to readily access allylic quaternary stereocenters with substituted internal alkenes and a variety of functional groups and heteroatoms in high yield and enantioenrichment Advisors/Committee Members: Watson, Mary P..

Subjects/Keywords: Pure sciences; Benzylic ammonium triflates; Enantioenriched benzylic boronates; N-heterocyclic carbene

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APA (6^th Edition):

Cobb, K. M. (2017). Stereospecific, nickel-catalyzed cross-couplings of amine and alcohol derived substrates. (Doctoral Dissertation). University of Delaware. Retrieved from http://udspace.udel.edu/handle/19716/21815

Chicago Manual of Style (16^th Edition):

Cobb, Kelsey M. “Stereospecific, nickel-catalyzed cross-couplings of amine and alcohol derived substrates.” 2017. Doctoral Dissertation, University of Delaware. Accessed April 18, 2021. http://udspace.udel.edu/handle/19716/21815.

MLA Handbook (7^th Edition):

Cobb, Kelsey M. “Stereospecific, nickel-catalyzed cross-couplings of amine and alcohol derived substrates.” 2017. Web. 18 Apr 2021.

Vancouver:

Cobb KM. Stereospecific, nickel-catalyzed cross-couplings of amine and alcohol derived substrates. [Internet] [Doctoral dissertation]. University of Delaware; 2017. [cited 2021 Apr 18]. Available from: http://udspace.udel.edu/handle/19716/21815.

Council of Science Editors:

Cobb KM. Stereospecific, nickel-catalyzed cross-couplings of amine and alcohol derived substrates. [Doctoral Dissertation]. University of Delaware; 2017. Available from: http://udspace.udel.edu/handle/19716/21815

Colorado State University

13. Dunn, Eric F. Investigation into discrete molecular catalysts for biomass conversion into 5-hydroxymethylfurfural.

Degree: MS(M.S.), Chemistry, 2013, Colorado State University

URL: http://hdl.handle.net/10217/80234

► As part of ongoing research into the conversion of biomass into the platform chemical 5-hydroxymethylfurfural (HMF), two primary investigations have been performed. The first is… (more)

Subjects/Keywords: 5-hydroxymethylfurfural; biomass; chromium; glucose; Ionic liquids; N-heterocyclic carbene

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APA (6^th Edition):

Dunn, E. F. (2013). Investigation into discrete molecular catalysts for biomass conversion into 5-hydroxymethylfurfural. (Masters Thesis). Colorado State University. Retrieved from http://hdl.handle.net/10217/80234

Chicago Manual of Style (16^th Edition):

Dunn, Eric F. “Investigation into discrete molecular catalysts for biomass conversion into 5-hydroxymethylfurfural.” 2013. Masters Thesis, Colorado State University. Accessed April 18, 2021. http://hdl.handle.net/10217/80234.

MLA Handbook (7^th Edition):

Dunn, Eric F. “Investigation into discrete molecular catalysts for biomass conversion into 5-hydroxymethylfurfural.” 2013. Web. 18 Apr 2021.

Vancouver:

Dunn EF. Investigation into discrete molecular catalysts for biomass conversion into 5-hydroxymethylfurfural. [Internet] [Masters thesis]. Colorado State University; 2013. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/10217/80234.

Council of Science Editors:

Dunn EF. Investigation into discrete molecular catalysts for biomass conversion into 5-hydroxymethylfurfural. [Masters Thesis]. Colorado State University; 2013. Available from: http://hdl.handle.net/10217/80234

University of Iowa

14. Bemowski, Ross David. Novel N-heterocyclic dicarbene ligands and molybdenum and dimolybdenum N-heterocyclic carbene complexes.

Degree: PhD, Chemistry, 2013, University of Iowa

URL: https://ir.uiowa.edu/etd/1291

► The syntheses of a new class of polycyclic TriAmino DiCarbenes (TADCs), based on 3,9-diazajulolidine, and their precursors and adducts are described. Starting with 2,6-dimethyl-nitrobenzene,… (more)

▼ The syntheses of a new class of polycyclic TriAmino DiCarbenes (TADCs), based on 3,9-diazajulolidine, and their precursors and adducts are described. Starting with 2,6-dimethyl-nitrobenzene, 2,6-bis ((alkylamino)methyl)anilines (alkyl = isopropyl, mesityl, and tert-butyl) were synthesized in 40% yield over five steps. These triamines were then di-cyclized stepwise to diformamidinium dications or formamidinium/2-methoxyformaminals using oxonium salts and trialkyl orthoformates. A diformamidinium dication was characterized by single-crystal X-ray diffractometry. Treatment with various bases, particularly lithium hexamethyldisilylazide, led to the novel TADCs and monocarbenes, two of which were isolated and characterized by 1H and 13C NMR spectroscopies. In both cases, treatment with elemental sulfur trapped the TADCs as dithiobiurets. No TADC-transition metal complexes were successfully isolated from reactions of the diformamidinium dications or LiHMDS TADC complex with a number of transition metal complexes. With the exception of these two cases, all other TADCs were not isolated because they rapidly reacted to form dimers, trimers, and tetramers. One of these dimers was isolated and its structure determined using 1D and 2D NMR spectroscopies, along with high-resolution electrospray ionization mass spectrometry. This revealed that the TADC had dimerized to form an ene-triamine, likely via 1,3-shift of a benzylic proton. Novel N-heterocyclic Carbene (NHC) complexes of molybdenum were also synthesized and characterized. Reaction of Cp2Mo2(CO)4 (Cp = C5H5) with dimesityl-imidazol-2-ylidenes (IMes) or dimesityl-imidazolidin-2-ylidenes (SIMes) yielded the molybdoradicals CpMo(CO)2(NHC) (NHC = IMes or SIMes). The carbonyl infrared stretching frequencies and the relative metal-to-NHC π-backbonding for IMes and SIMes complexes are compared. Reaction of the less bulky dimethyl-imidazol-2-ylidene (IMe) with Cp2Mo2(CO)4 yielded the Mo-Mo triple bond complex Cp2Mo2(CO)3(IMe) by CO substitution. This is the first example of an NHC-ligated metal-metal multiply bonded complex. Single crystal X-ray diffractometry of these new organomolybdenum and organodimolybdenum complexes is discussed. Advisors/Committee Members: Messerle, Louis (supervisor).

Subjects/Keywords: Metal-Metal multiple bonds; Molybdenum; N-Heterocyclic carbene; Chemistry

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APA (6^th Edition):

Bemowski, R. D. (2013). Novel N-heterocyclic dicarbene ligands and molybdenum and dimolybdenum N-heterocyclic carbene complexes. (Doctoral Dissertation). University of Iowa. Retrieved from https://ir.uiowa.edu/etd/1291

Chicago Manual of Style (16^th Edition):

Bemowski, Ross David. “Novel N-heterocyclic dicarbene ligands and molybdenum and dimolybdenum N-heterocyclic carbene complexes.” 2013. Doctoral Dissertation, University of Iowa. Accessed April 18, 2021. https://ir.uiowa.edu/etd/1291.

MLA Handbook (7^th Edition):

Bemowski, Ross David. “Novel N-heterocyclic dicarbene ligands and molybdenum and dimolybdenum N-heterocyclic carbene complexes.” 2013. Web. 18 Apr 2021.

Vancouver:

Bemowski RD. Novel N-heterocyclic dicarbene ligands and molybdenum and dimolybdenum N-heterocyclic carbene complexes. [Internet] [Doctoral dissertation]. University of Iowa; 2013. [cited 2021 Apr 18]. Available from: https://ir.uiowa.edu/etd/1291.

Council of Science Editors:

Bemowski RD. Novel N-heterocyclic dicarbene ligands and molybdenum and dimolybdenum N-heterocyclic carbene complexes. [Doctoral Dissertation]. University of Iowa; 2013. Available from: https://ir.uiowa.edu/etd/1291

University of Houston

15. Zhao, Yang 1987-. Synthesis of Proline-Based N-Heterocyclic Carbene Building Blocks and Their Applications.

Degree: PhD, Chemistry, 2015, University of Houston

URL: http://hdl.handle.net/10657/1936

► The synthesis of novel proline-based N-heterocyclic carbene ligands has been accomplished. These types of imidazolium salts can be used as building blocks for the synthesis… (more)

Subjects/Keywords: Synthesis; N-heterocyclic carbene; Amino acid; Peptide; Ligands; Catalysis

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APA (6^th Edition):

Zhao, Y. 1. (2015). Synthesis of Proline-Based N-Heterocyclic Carbene Building Blocks and Their Applications. (Doctoral Dissertation). University of Houston. Retrieved from http://hdl.handle.net/10657/1936

Chicago Manual of Style (16^th Edition):

Zhao, Yang 1987-. “Synthesis of Proline-Based N-Heterocyclic Carbene Building Blocks and Their Applications.” 2015. Doctoral Dissertation, University of Houston. Accessed April 18, 2021. http://hdl.handle.net/10657/1936.

MLA Handbook (7^th Edition):

Zhao, Yang 1987-. “Synthesis of Proline-Based N-Heterocyclic Carbene Building Blocks and Their Applications.” 2015. Web. 18 Apr 2021.

Vancouver:

Zhao Y1. Synthesis of Proline-Based N-Heterocyclic Carbene Building Blocks and Their Applications. [Internet] [Doctoral dissertation]. University of Houston; 2015. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/10657/1936.

Council of Science Editors:

Zhao Y1. Synthesis of Proline-Based N-Heterocyclic Carbene Building Blocks and Their Applications. [Doctoral Dissertation]. University of Houston; 2015. Available from: http://hdl.handle.net/10657/1936

Boston College

16. O'Brien, Jeannette M. New Catalysts and Catalytic Methods for Cycloadditions and Conjugate Additions to Alpha, Beta-Unsaturated Carbonyls.

Degree: PhD, Chemistry, 2012, Boston College

URL: http://dlib.bc.edu/islandora/object/bc-ir:103617

► Chapter 1. A Practical Synthesis of 3-Acyl Cyclobutanones by [2 + 2] Annulation. Mechanism and Utility of the Zn(II)-Catalyzed Condensation of alpha-Chloroenamines with Electron-Deficient Alkenes.… (more)

▼ Chapter 1. A Practical Synthesis of 3-Acyl Cyclobutanones by [2 + 2] Annulation. Mechanism and Utility of the Zn(II)-Catalyzed Condensation of alpha-Chloroenamines with Electron-Deficient Alkenes. We have developed a catalytic method for the synthesis of highly functionalized 3-acyl cyclobutanones which are useful building blocks for a variety of natural products. Methods for cyclobutanone synthesis have traditionally been limited to Lewis-acid promoted rearrangement of oxaspiropentanes or cyclizations of ketene and syntheses involving keteneiminium salts have required stoichiometric quantities of a Lewis acid. Furthermore, the mechanism for these types of cyclizations remains unknown. This portion of my research focused on an efficient, catalytic method for the synthesis of 3- acyl cyclobutanones and providing insight into the mechanism for cycloaddition. Chapter 2. Enantioselective Synthesis of Boron-Substituted Quaternary Carbons by NHC-Cu-Catalyzed Boronate Conjugate Additions to Unsaturated Carboxylic Esters, Ketones, or Thioesters. We have developed an enantioselective NHC-Cu-catalyzed conjugate addition of boronate esters to acyclic, trisubstituted alpha, beta-unsaturated carbonyl compounds. Enantioselective conjugate addition of a boronic acid pinacol ester through the use of bis(pinacolato)diboron [B2(pin)2,] to alpha, beta-unsaturated aliphatic and aryl esters promoted by 5 mol % of an NHC-Cu catalyst afforded tertiary beta-boryl carbonyls in high efficiency and enantioselectivity. Trisubstituted alpha, beta-unsaturated esters and thioesters were found to be reactive substrates in the presence of a stoichiometric quantity of methanol. Chapter 3. Metal-Free Catalytic C-Si Bond Formation in an Aqueous Medium and C-B Bond Formation in a Protic Medium. Enantioselective NHC-Catalyzed Silyl and Boryl Conjugate Additions to Cyclic and Acyclic alpha, beta-Unsaturated carbonyls. We have developed a method for enantioselective metal-free silyl conjugate additions through the use of dimethylphenylsilyl) boronic acid pinacol ester [PhMe2SiB(pin)] catalyzed by chiral N-heterocyclic carbenes (NHCs) in basic aqueous thf. Optimization of metal-free conditions demonstrated that the presence of water was required for high efficiency. alpha, beta-Unsaturated cyclic ketones and lactones were examined as substrates, and acyclic ketones, esters and aldehydes were also competent substrates for silyl conjugate addition. beta-Silyl carbonyls were isolated in up to >98% yield and >98:2 er. Chapter 4. Elucidation of Mechanism for Enantioselective NHC-Catalyzed Silyl Conjugate Addition. We propose a catalytic cycle for NHC-catalyzed enantioselective silyl conjugate addition. Mechanistic studies of NHC-catalyzed enantioselective silyl conjugate additions are presented. Optimization of conditions for an inefficient alpha, beta-unsaturated electron-deficient ketone provided insight into the roles for dbu and water. Kinetic data indicate that conjugate addition is first order in PhMe2SiB(pin) and carbene, and DFT calculations support the… Advisors/Committee Members: Marc L. Snapper (Thesis advisor).

Subjects/Keywords: Boron; Conjugate Addition; Keteneiminium; NHC; N-Heterocyclic Carbene; Silicon

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

O'Brien, J. M. (2012). New Catalysts and Catalytic Methods for Cycloadditions and Conjugate Additions to Alpha, Beta-Unsaturated Carbonyls. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:103617

Chicago Manual of Style (16^th Edition):

O'Brien, Jeannette M. “New Catalysts and Catalytic Methods for Cycloadditions and Conjugate Additions to Alpha, Beta-Unsaturated Carbonyls.” 2012. Doctoral Dissertation, Boston College. Accessed April 18, 2021. http://dlib.bc.edu/islandora/object/bc-ir:103617.

MLA Handbook (7^th Edition):

O'Brien, Jeannette M. “New Catalysts and Catalytic Methods for Cycloadditions and Conjugate Additions to Alpha, Beta-Unsaturated Carbonyls.” 2012. Web. 18 Apr 2021.

Vancouver:

O'Brien JM. New Catalysts and Catalytic Methods for Cycloadditions and Conjugate Additions to Alpha, Beta-Unsaturated Carbonyls. [Internet] [Doctoral dissertation]. Boston College; 2012. [cited 2021 Apr 18]. Available from: http://dlib.bc.edu/islandora/object/bc-ir:103617.

Council of Science Editors:

O'Brien JM. New Catalysts and Catalytic Methods for Cycloadditions and Conjugate Additions to Alpha, Beta-Unsaturated Carbonyls. [Doctoral Dissertation]. Boston College; 2012. Available from: http://dlib.bc.edu/islandora/object/bc-ir:103617

Boston College

17. McGrath, Kevin Patrick. Enantioselective Methods for Allylic Substitution and Conjugate Addition Reactions Catalyzed by N-Heterocyclic Carbene-Copper Complexes.

Degree: PhD, Chemistry, 2016, Boston College

URL: http://dlib.bc.edu/islandora/object/bc-ir:106792

► Chapter 1 Catalytic Enantioselective Addition of Organoaluminum Reagents Catalytic methods involving the enantioselective addition of both commercially available as well as in situ generated organoaluminum… (more)

▼ Chapter 1 Catalytic Enantioselective Addition of Organoaluminum Reagents Catalytic methods involving the enantioselective addition of both commercially available as well as in situ generated organoaluminum reagents are reviewed. An overview of additions to aldehydes, ketones, and imines is provided as well as the difficulties and limitations of such transformations. Furthermore, additions to unsaturation adjacent to a leaving group to form a new stereogenic center are examined. Finally, conjugate addition reactions wherein an organoaluminum reagent is added to an olefin adjacent to a carbonyl or nitro group are discussed. Chapter 2 Synthesis of Quaternary Carbon Stereogenic Centers through Enantioselective Cu-Catalyzed Allylic Substitution with Alkenylaluminum Reagents A method for the formation of 1,4-diene containing quaternary stereogenic centers through catalytic enantioselective allylic substitution is disclosed. The addition of alkyl- and aryl-substituted alkenylaluminum reagents to trisubstituted allylic phosphates is promoted by 0.5–2.5 mol % of a sulfonate-containing bidentate N-heterocyclic carbene–copper complex. Products containing a quaternary stereogenic center as well as a newly formed terminal olefin are obtained in up to 97% yield and 99:1 er with high site selectivity (>98:2 SN2’:SN2). The requisite nucleophiles are generated in situ through hydroalumination of terminal alkynes. The utility of the method is demonstrated through a concise synthesis of natural product bakuchiol. Chapter 3 A Multicomponent Ni-, Zr-, Cu-Catalyzed Strategy for Enantioselective Synthesis of Alkenyl-Substituted Quaternary Carbons Despite the widespread use of conjugate addition in organic synthesis, few reports pertain to the addition of nucleophiles to acyclic systems and none in which the nucleophile is an alkene. Herein, we report the first examples of enantioselective conjugate addition of alkenylmetal reagents to trisubstituted enones to form all-carbon quaternary stereogenic centers. Alkenylaluminum nucleophiles are prepared through a site-selective Ni-catalyzed hydroalumination of terminal alkynes and the requisite E-trisubsituted enones are the products of a regioselective Zr-catalyzed carboalumination/acylation of a terminal alkyne. Products are obtained in up to 97% yield and 99:1 er. A model for enantioselectivity, supported by DFT calculations, is proposed. Chapter 4 Formation of Tertiary Centers through Catalytic Enantioselective Conjugate Addition of Alkenylaluminum Reagents to Acyclic Enones We have developed an enantioselective NHC–Cu catalyzed synthesis of tertiary centers in acyclic systems using in situ generated alkenylaluminum reagents, as current methods typically rely on Rh-catalysis at high temperatures with alkenyl boronic acids in protic solvents. Moreover, most examples include chalcone-derived substrates, which, while more reactive, often preclude further functionalization. With the current method, we are able to couple a variety of alkenyl nucleophiles with α,β-unsaturated ketones. E- or… Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).

Subjects/Keywords: Allylic Substitution; Conjugate Addition; Copper; Enantioselective; N-Heterocyclic Carbene; Organoaluminum

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APA (6^th Edition):

McGrath, K. P. (2016). Enantioselective Methods for Allylic Substitution and Conjugate Addition Reactions Catalyzed by N-Heterocyclic Carbene-Copper Complexes. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:106792

Chicago Manual of Style (16^th Edition):

McGrath, Kevin Patrick. “Enantioselective Methods for Allylic Substitution and Conjugate Addition Reactions Catalyzed by N-Heterocyclic Carbene-Copper Complexes.” 2016. Doctoral Dissertation, Boston College. Accessed April 18, 2021. http://dlib.bc.edu/islandora/object/bc-ir:106792.

MLA Handbook (7^th Edition):

McGrath, Kevin Patrick. “Enantioselective Methods for Allylic Substitution and Conjugate Addition Reactions Catalyzed by N-Heterocyclic Carbene-Copper Complexes.” 2016. Web. 18 Apr 2021.

Vancouver:

McGrath KP. Enantioselective Methods for Allylic Substitution and Conjugate Addition Reactions Catalyzed by N-Heterocyclic Carbene-Copper Complexes. [Internet] [Doctoral dissertation]. Boston College; 2016. [cited 2021 Apr 18]. Available from: http://dlib.bc.edu/islandora/object/bc-ir:106792.

Council of Science Editors:

McGrath KP. Enantioselective Methods for Allylic Substitution and Conjugate Addition Reactions Catalyzed by N-Heterocyclic Carbene-Copper Complexes. [Doctoral Dissertation]. Boston College; 2016. Available from: http://dlib.bc.edu/islandora/object/bc-ir:106792

Boston College

18. Lee, Yunmi. Site- and Enantioselective C-C and C-B Bond Forming Reactions Catalyzed by Cu-, Mg-, Zn-, or Al-based N-Heterocyclic Carbene Complexes.

Degree: PhD, Chemistry, 2010, Boston College

URL: http://dlib.bc.edu/islandora/object/bc-ir:101999

► Chapter 1. In this chapter, the ability of chiral bidentate N-heterocyclic carbenes (NHCs) to activate alkylmetal reagents directly in order to promote C‒C bond forming… (more)

▼ Chapter 1. In this chapter, the ability of chiral bidentate N-heterocyclic carbenes (NHCs) to activate alkylmetal reagents directly in order to promote C‒C bond forming reactions in the absence of a Cu salt is presented. Highly regio- and enantioselective Cu-free allylic alkylation reactions of di- and trisubstituted allylic substrates with organomagnesium, organozinc, and organoaluminum reagents are demonstrated. Chiral bidentate sulfonate-bearing NHC-Zn and NHC-Al complexes are isolated and fully characterized. Based on crystal structures of these catalytic complexes, mechanistic details regarding Cu-free allylic alkylations with alkylmetal reagents are proposed. Chapter 2. New methods for efficient and highly enantioselective Cu-catalyzed allylic alkylation reactions of a variety of trisubstituted allylic substrates with alkylmagnesium and alkyl-, aryl-, 2-furyl-, and 2-thiophenylaluminum reagents are presented. Transformations are promoted by a chiral NHC complex in the presence of commercially available, inexpensive and air stable CuCl2*H2O. Enantiomerically enriched compounds containing difficult-to-access all-carbon quaternary stereogenic centers are obtained. Chapter 3. New methods for highly site- and enantioselective Cu-catalyzed allylic alkylation reactions of allylic phosphates with vinylaluminum reagents are presented. The requisite vinylaluminums are prepared by reaction of readily accessible terminal alkynes with DIBAL-H and used directly without further purification. Vinyl additions are promoted in the presence of a chiral bidentate sulfonate-based NHC complex and a Cu salt. The desired SN2' products are obtained in >98% E selectivities, >98% SN2' selectivities, >98% group selectivities (<2% i-Bu addition) and high enantioselectivities. The enantioselective total synthesis of the natural product bakuchiol highlights the versatility of the one-pot hydroalumination/Cu-catalyzed enantioselective allylic vinylation process. Chapter 4. Efficient and highly site-selective Cu-catalyzed hydroboration reactions of 1,2-disubstituted aryl olefins with bis(pinacolato)diboron (B2(pin)2) are presented. Transformations are promoted by an NHC-Cu complex in the presence of MeOH, affording only secondary β-boronate isomers. A Cu-catalyzed method for the synthesis of enantiomerically enriched secondary alkylboronates promoted by chiral NHC complexes is disclosed. Chapter 5. A new method for efficient and site-selective tandem Cu-catalyzed copper-boron additions to terminal alkynes with B2(pin)2 in the presence of an NHC-Cu complex is demonstrated. In a one-pot process, Cu-catalyzed hydroboration of alkynes provides vinylboronates in situ, which undergo a second site-selective hydroboration to afford vicinal diboronates. Highly Enantiomerically enriched diboronates obtained through Cu-catalyzed enantioselective dihydroboration in the presence of chiral bidentate sulfonate-based NHC-Cu complex are obtained. The control of site selectivity in the first-stage hydroboration of alkynes is critical for efficient and… Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).

Subjects/Keywords: Cu-catalyzed reaction; Dihydroboration; Enantioselective Allylic Alkylation; Hydroboration; N-Heterocyclic carbene

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Lee, Y. (2010). Site- and Enantioselective C-C and C-B Bond Forming Reactions Catalyzed by Cu-, Mg-, Zn-, or Al-based N-Heterocyclic Carbene Complexes. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101999

Chicago Manual of Style (16^th Edition):

Lee, Yunmi. “Site- and Enantioselective C-C and C-B Bond Forming Reactions Catalyzed by Cu-, Mg-, Zn-, or Al-based N-Heterocyclic Carbene Complexes.” 2010. Doctoral Dissertation, Boston College. Accessed April 18, 2021. http://dlib.bc.edu/islandora/object/bc-ir:101999.

MLA Handbook (7^th Edition):

Lee, Yunmi. “Site- and Enantioselective C-C and C-B Bond Forming Reactions Catalyzed by Cu-, Mg-, Zn-, or Al-based N-Heterocyclic Carbene Complexes.” 2010. Web. 18 Apr 2021.

Vancouver:

Lee Y. Site- and Enantioselective C-C and C-B Bond Forming Reactions Catalyzed by Cu-, Mg-, Zn-, or Al-based N-Heterocyclic Carbene Complexes. [Internet] [Doctoral dissertation]. Boston College; 2010. [cited 2021 Apr 18]. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101999.

Council of Science Editors:

Lee Y. Site- and Enantioselective C-C and C-B Bond Forming Reactions Catalyzed by Cu-, Mg-, Zn-, or Al-based N-Heterocyclic Carbene Complexes. [Doctoral Dissertation]. Boston College; 2010. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101999

Boston College

19. Gao, Fang. Copper-Catalyzed Enantioselective Allylic Substitution Reactions with Organoaluminum and Boron Based Reagents Promoted by Chiral Sulfonate Bearing N-Heterocyclic Carbenes.

Degree: PhD, Chemistry, 2013, Boston College

URL: http://dlib.bc.edu/islandora/object/bc-ir:101227

► Chapter 1. A Review of Catalytic Enantioselective Allylic Substitution (EAS) with Chiral Sulfonate Containing N-heterocyclic Carbenes (NHC). A comprehensive review of enantioselective allylic substitution reactions,… (more)

▼ Chapter 1. A Review of Catalytic Enantioselective Allylic Substitution (EAS) with Chiral Sulfonate Containing N-heterocyclic Carbenes (NHC). A comprehensive review of enantioselective allylic substitution reactions, which are promoted by a chiral N-heterocyclic carbene metal complex that features a unique sulfonate motif, is provided in this chapter. Reactions are classified into two categories. One class of transformations is catalyzed by a series of easily modifiable sulfonate bearing NHC-Cu complexes, with which a range of nucleophilic organometallic reagents (i.e., organozinc-, aluminum-, magnesium- and boron-based) that carry different carbon-based units are readily utilized in efficient and highly selective C-C bond forming processes. Another set of reactions exclude the use of a copper salt; catalytic amount of a sulfonate containing imidazolinium salt is capable of promoting additions of alkyl Grignard, zinc and aluminum species to easily available allylic electrophiles in a site- and enantioselective fashion. The mechanistic scenarios of both catalytic systems that account for the observed experimental data are discussed in detail. Chapter 2. Cu-Catalyzed Enantioselective Allylic Substitutions with Aryl- and Heteroarylaluminum Reagents. In this chapter, the first examples of EAS reactions of aryl- and heteroaryl-substituted dialkylaluminum reagents to a wide range of trisubstituted allylic phosphates are demonstrated through a facile and selective catalysis rendered possible by an in situ generated sulfonate containing NHC-Cu complex, delivering enantiomerically enriched olefin products that bear an all carbon quaternary stereogenic center. The requisite organometallic species are easily prepared from either the corresponding aryl- and heteroaryl halides, or through efficient and site selective deprotonation at the C-2 position of furan and thiophene; such aluminum entities are readily used in situ without the requirement of purification. Application to small molecule natural product synthesis is also carried out to illustrate the utility of the present protocol. Chapter 3. Cu-Catalyzed Enantioselective Allylic Substitutions with Alkenylaluminum Reagents. This chapter focuses on our research towards construction of enantioenriched tertiary and quaternary stereogenic centers that are substituted with two further functionalizable alkenes. The first combination of the study involves the addition of stereochemically well-defined trisubstituted alkenylaluminum reagents to disubstituted allylic phosphates; the transformation commences with a silyl-directed stereoselective hydroalumination and finishes with an enantioselective Cu-catalyzed EAS promoted by a sulfonate bearing NHC. Such reactions deliver molecules that feature silicon containing trisubstituted olefin adjacent to the tertiary stereogenic center; subsequent conversion of the versatile silicon group to a proton reveals the first set of examples that incorporate pure Z alkene in Cu-catalyzed EAS. The stereoselective and concise synthesis of naturally… Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).

Subjects/Keywords: Allylic Substitution; Aluminum; Boron; Copper; Enantioselective; N-heterocyclic carbene

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Gao, F. (2013). Copper-Catalyzed Enantioselective Allylic Substitution Reactions with Organoaluminum and Boron Based Reagents Promoted by Chiral Sulfonate Bearing N-Heterocyclic Carbenes. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101227

Chicago Manual of Style (16^th Edition):

Gao, Fang. “Copper-Catalyzed Enantioselective Allylic Substitution Reactions with Organoaluminum and Boron Based Reagents Promoted by Chiral Sulfonate Bearing N-Heterocyclic Carbenes.” 2013. Doctoral Dissertation, Boston College. Accessed April 18, 2021. http://dlib.bc.edu/islandora/object/bc-ir:101227.

MLA Handbook (7^th Edition):

Gao, Fang. “Copper-Catalyzed Enantioselective Allylic Substitution Reactions with Organoaluminum and Boron Based Reagents Promoted by Chiral Sulfonate Bearing N-Heterocyclic Carbenes.” 2013. Web. 18 Apr 2021.

Vancouver:

Gao F. Copper-Catalyzed Enantioselective Allylic Substitution Reactions with Organoaluminum and Boron Based Reagents Promoted by Chiral Sulfonate Bearing N-Heterocyclic Carbenes. [Internet] [Doctoral dissertation]. Boston College; 2013. [cited 2021 Apr 18]. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101227.

Council of Science Editors:

Gao F. Copper-Catalyzed Enantioselective Allylic Substitution Reactions with Organoaluminum and Boron Based Reagents Promoted by Chiral Sulfonate Bearing N-Heterocyclic Carbenes. [Doctoral Dissertation]. Boston College; 2013. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101227

20. Fyfe, Andrew Alston. d- and f-metal alkoxy-tethered N-heterocyclic carbene complexes.

Degree: PhD, 2016, University of Edinburgh

URL: http://hdl.handle.net/1842/15862

► Chapter one is an introduction, outlining the structure and bonding of N-heterocyclic carbenes (NHCs). It then goes on to give examples of f -metal NHC… (more)

▼ Chapter one is an introduction, outlining the structure and bonding of N-heterocyclic carbenes (NHCs). It then goes on to give examples of f -metal NHC complexes and describes any reactivity or catalytic activity. Chapter two describes the synthesis of the transition metal NHC complexes [Fe (LMes)2] 3 and [Co(LMes)2] 4 (LMes = OCMe2 CH2(1-C{NCH2CH2NMes})). The heterobimetallic complexes [(LMes)Fe(μ-LMes)U(μ-{N(SiMe3)Si(Me)2CH2})(N(Si Me3)2)2] 5 and [(LMes)Co(μ-LMes)U(μ-{N(SiMe3)Si(Me)2CH2})(N(SiMe3)2)2] 6 were prepared from the reaction between [({Me3Si}2N)2U(NSiMe3SiMe2CH2)] and 3 or 4, respectively. Complex 5 was also synthesised by the reaction between 3 and [U(N{SiMe3}2)2]. The diamagnetic analogue [(LMes)Zn(μ-LMes)Th(μ-{N(SiMe3)Si (Me)2CH2})(N(SiMe3)2)2] 9 was prepared from the reaction between [Zn(LMes)2] and [({SiMe3}2N)2Th(NSiMe3SiMe2CH2)]. The reactivity of 5 is discussed. When 5 was reacted with 2,6-dimethylphenyl isocyanide, [({SiMe3}2N)2U{N(SiMe3)Si(Me2)C(CH2)N(2,6−Me−C6H3)}] 8 was isolated. The reaction with CO resulted in the formation of [({Me3Si}2N)2U{N(SiMe3) Si(Me2)C(CH2)CO}]. 5 showed no reactivity with azides, boranes or m-chloroperbenzoic acid and decomposed when exposed to H2, CO2 or KC8. The reaction between 6 and 2,6-di-tert-butylphenol formed the previously reported monometallic complex [({SiMe3}2N)2U(OC6H3tBu2)]. The serendipitous synthesis of the iron ate complex [Na(Fe{LMes}2)2]+ [Fe(ArO)3]– 10 (Ar = 2,6-tBu-C6H3) is also described. Chapter three describes the synthesis of the aryloxide complexes [HC(3-tBu-5-Me- C6H2OH)(3-tBu-5-Me-C6H2O)μ-(3-tBu-5-Me-C6H2O)Co(THF)]2 11 and [HC(3- tBu-5-Me-C6H2OH)(3-tBu-5-Me-C6H2O)μ-(3-tBu-5-Me-C6H2O)Zn(THF)n] 13. Treatment of 11 with pyridine N-oxide resulted in the formation of the pyridine-Noxide adduct [HC(3-tBu-5-Me-C6H2OH)(3-tBu-5-Me-C6H2O)μ-(3-tBu-5-Me-C6H2 O)Co(C5H5NO)]2 12. When 11 was treated with [({Me3Si}2N)2U(NSiMe3SiMe2C H2)], no reaction occured at room temperature but at 80◦C decomposition occured. When 11 was treated with [(NH4)2Ce(NO3)6] the protonated proligand HC(3-tBu- 5-Me-C6H2OH)3 reformed. The reactivity of 11 with [({Me3Si}2N)Ce(LiPr)2] is also discussed. Chapter three also discusses the preparation of the heterobimetallic complex [HC(3- tBu-5-Me-C6H2O)2-μ-(3-tBu-5-Me-C6H2O)KCo]2 14 and the salt-elimination chemistry of the complex. The preparation of [HC(3-tBu-5-Me-C6H2O)2-μ-(3-tBu-5- Me-C6H2O)KZn]2 15 is also outlined. Chapter four discusses the reactivity of [Ce(LiPr)3] (Li Pr =OCMe2CH2(1-C{NCHC HNiPr})) in C-H and N-H activation and as a catalyst for organic reactions. [Ce(LiPr)3] displayed no C-H activation chemistry with RC−−−CH (R = SiMe3, Ph, tBu), diphenyl acetone, indene or fluorene. [Ce(LiPr)3] also showed no N-H activation chemistry with pyrrole or indole, nor did it react with the lignin model compound PhOCH2Ph. When treated with an excess of benzyl chloride, [Ce(LiPr)3] underwent ligand decomposition to form the acylazolium chloride [(C6H5C(O))OCMe2CH2(1-C(C6H5C (O)){NCHCHNiPr})]Cl 18 and CeCl3. When [Ce(LiPr)3] was…

Subjects/Keywords: 547; actinide; N-heterocyclic carbene; NHC; bimetallic; heterobimetallic; C-H activation

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Fyfe, A. A. (2016). d- and f-metal alkoxy-tethered N-heterocyclic carbene complexes. (Doctoral Dissertation). University of Edinburgh. Retrieved from http://hdl.handle.net/1842/15862

Chicago Manual of Style (16^th Edition):

Fyfe, Andrew Alston. “d- and f-metal alkoxy-tethered N-heterocyclic carbene complexes.” 2016. Doctoral Dissertation, University of Edinburgh. Accessed April 18, 2021. http://hdl.handle.net/1842/15862.

MLA Handbook (7^th Edition):

Fyfe, Andrew Alston. “d- and f-metal alkoxy-tethered N-heterocyclic carbene complexes.” 2016. Web. 18 Apr 2021.

Vancouver:

Fyfe AA. d- and f-metal alkoxy-tethered N-heterocyclic carbene complexes. [Internet] [Doctoral dissertation]. University of Edinburgh; 2016. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/1842/15862.

Council of Science Editors:

Fyfe AA. d- and f-metal alkoxy-tethered N-heterocyclic carbene complexes. [Doctoral Dissertation]. University of Edinburgh; 2016. Available from: http://hdl.handle.net/1842/15862

21. Helgert, Theodore Rudy. Early Transition Metal CCC-NHC Pincer Complexes: Synthesis, Characterization, and Catalysis.

Degree: PhD, Chemistry and Biochemistry, 2013, University of Mississippi

URL: https://egrove.olemiss.edu/etd/1364

► The previously reported amine elimination methodology for the metalation of CCC-NHC pincer ligand precursors has been extended to other early-transition metals and ligands. Specifically, synthetic… (more)

Subjects/Keywords: CCC-NHC; N-Heterocyclic Carbene; Pincer; Tantalum; Titanium; Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Helgert, T. R. (2013). Early Transition Metal CCC-NHC Pincer Complexes: Synthesis, Characterization, and Catalysis. (Doctoral Dissertation). University of Mississippi. Retrieved from https://egrove.olemiss.edu/etd/1364

Chicago Manual of Style (16^th Edition):

Helgert, Theodore Rudy. “Early Transition Metal CCC-NHC Pincer Complexes: Synthesis, Characterization, and Catalysis.” 2013. Doctoral Dissertation, University of Mississippi. Accessed April 18, 2021. https://egrove.olemiss.edu/etd/1364.

MLA Handbook (7^th Edition):

Helgert, Theodore Rudy. “Early Transition Metal CCC-NHC Pincer Complexes: Synthesis, Characterization, and Catalysis.” 2013. Web. 18 Apr 2021.

Vancouver:

Helgert TR. Early Transition Metal CCC-NHC Pincer Complexes: Synthesis, Characterization, and Catalysis. [Internet] [Doctoral dissertation]. University of Mississippi; 2013. [cited 2021 Apr 18]. Available from: https://egrove.olemiss.edu/etd/1364.

Council of Science Editors:

Helgert TR. Early Transition Metal CCC-NHC Pincer Complexes: Synthesis, Characterization, and Catalysis. [Doctoral Dissertation]. University of Mississippi; 2013. Available from: https://egrove.olemiss.edu/etd/1364

University of Toronto

22. Wan, Kai Yang. Chiral Donor-Functionalized N-Heterocyclic Carbenes for Asymmetric Catalytic Applications in Hydrogenation – From Design to Application.

Degree: PhD, 2018, University of Toronto

URL: http://hdl.handle.net/1807/95725

►

In this thesis, the synthetic protocol for a new class of enantiopure, primary-amine tethered N-heterocyclic carbene (NHC) ligands is described. The synthesis, coordination chemistry, and… (more)

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In this thesis, the synthetic protocol for a new class of enantiopure, primary-amine tethered N-heterocyclic carbene (NHC) ligands is described. The synthesis, coordination chemistry, and applications in catalysis for three ligands from this class with general formula (S,S)/(R,R)-H2N-CHPh-CHPh-NHC (NHC = -NCHCHN(C)R, R = Me, tBu, or Mes) are reported. The imidazolium salt of these ligands can be prepared in high yield and purity from the SN1 reaction between chiral sulfamidates and the corresponding N-substituted imidazoles. The method of coordination of the NHC ligands to metals depends on the acidity of the C-H functional in the imidazolium salts. Silver and copper compounds can be prepared in high yield with the ligand to the metal ratio of 2:1 or 1:1. Ruthenium, iridium, and rhodium complexes can also be prepared via transmetallation from the silver or copper reagents, intramolecular base deprotonation, or C-H oxidative addition. Four ruthenium complexes and two iridium complexes based on these ligands were proven active for ketone hydrogenation, under relatively mild condition (50℃, 25 bar H2(g)). Three half-sandwich ruthenium compounds containing Cp (cyclopentadienyl) or Cp* (1,2,3,4,5-pentamethylcyclopentadienyl) are highly active aryl and alkyl hydrogenation catalysts with TOF (turnover frequency) up to 67 s-1, TON (turnover number) up to 104, and ee (enantiomeric excess) up to 86%. An experimental and computational study of the half-sandwich ruthenium systems suggests that the heterolytic splitting of dihydrogen over the metal-amido bond and hydride transfer from the catalyst to the substrate can both be rate-determining. An alcohol-assisted mechanism was also calculated to explain the rate enhancement when the catalysis was conducted in polar, protic solvents such as 2-PrOH. A full experimental and computational study was also performed for a Fe(P-NH-P’) system. Similarly, heterolytic splitting and hydride transfer are the two most energy demanding transition states. In addition, the enantiodetermining step (EDS) of this asymmetric ketone hydrogenation catalyst was calculated, and the origins of enantioselectivity were summarized as steric repulsion, the high compressibility of the backbone, and H-bond contributed stabilization.

2019-07-11 00:00:00

Advisors/Committee Members: Morris, Robert H, Chemistry.

Subjects/Keywords: Asymmetric Catalysis; Chirality; Computational Chemistry; Hydrogenation; Kaibene; N-Heterocyclic Carbene; 0488

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APA (6^th Edition):

Wan, K. Y. (2018). Chiral Donor-Functionalized N-Heterocyclic Carbenes for Asymmetric Catalytic Applications in Hydrogenation – From Design to Application. (Doctoral Dissertation). University of Toronto. Retrieved from http://hdl.handle.net/1807/95725

Chicago Manual of Style (16^th Edition):

Wan, Kai Yang. “Chiral Donor-Functionalized N-Heterocyclic Carbenes for Asymmetric Catalytic Applications in Hydrogenation – From Design to Application.” 2018. Doctoral Dissertation, University of Toronto. Accessed April 18, 2021. http://hdl.handle.net/1807/95725.

MLA Handbook (7^th Edition):

Wan, Kai Yang. “Chiral Donor-Functionalized N-Heterocyclic Carbenes for Asymmetric Catalytic Applications in Hydrogenation – From Design to Application.” 2018. Web. 18 Apr 2021.

Vancouver:

Wan KY. Chiral Donor-Functionalized N-Heterocyclic Carbenes for Asymmetric Catalytic Applications in Hydrogenation – From Design to Application. [Internet] [Doctoral dissertation]. University of Toronto; 2018. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/1807/95725.

Council of Science Editors:

Wan KY. Chiral Donor-Functionalized N-Heterocyclic Carbenes for Asymmetric Catalytic Applications in Hydrogenation – From Design to Application. [Doctoral Dissertation]. University of Toronto; 2018. Available from: http://hdl.handle.net/1807/95725

23. Landers, Brant. N-Heterocyclic Carbene- and Antimony Pincer-Transition Metal Complexes: Their Synthesis and Catalytic Activity.

Degree: 2017, University of Hawaii – Manoa

URL: http://hdl.handle.net/10125/51210

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Ph.D. University of Hawaii at Manoa 2015.

Commercially available (N-heterocyclic carbene)-Pd ((NHC)-Pd) pre-catalysts were used for the anaerobic oxidation of secondary alcohols employing chloroarenes as… (more)

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Ph.D. University of Hawaii at Manoa 2015.

Commercially available (N-heterocyclic carbene)-Pd ((NHC)-Pd) pre-catalysts were used for the anaerobic oxidation of secondary alcohols employing chloroarenes as the oxidizing agent. The precatalyst (SIPr)Pd(cinnamyl)Cl (SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene) gave the best results showing drastic reductions in the reaction time and catalyst loading when compared to the counterpart bearing the analog unsaturated ligand. The catalytic system is compatible with the use of microwave dielectric heating, utilizing (IMes)Pd(allyl)Cl (IMes = 1,3-bis(2,4,6-trimethylphenyl)-imidazol-2-ylidene) as the pre-catalyst, where catalyst loading and reaction times can be decreased even further. Secondly, the use of microwave heating for the synthesis of a series of (NHC)Ni(Cp)Cl (Cp = Cyclopentadiene) complexes is presented. This protocol allows for a decrease in reaction time required using conventional heating, while affording comparable or better yields of the complexes bearing NHC ligands. Their application as pre-catalysts in the microwave-assisted anaerobic oxidation of secondary alcohols is also described. In addition, microwave heating is applied for the synthesis of NHC-bearing complexes of CuCl, AgCl, and AuCl. The use of microwave conditions allows for a reduction of the reaction times when compared to conventional heating, while still providing suitable yields of the desired (NHC)-metal-chloride complexes. Lastly, the synthesis of antimony ligands and their iridium(III) complexes is described. Two variations of bis-stibine ligands were prepared from either resorcinol or m-xylene and trichlorostibine. While the resorcinol variation, SbOCOSbtBu = 1,3-bis((ditert-butylstibino)-oxy)benzene, reacted with [Ir(COE)2Cl]2 to form a hydrido chloride complex, the resulting complex was coordinatively saturated with three stibine ligands. The bis-stibine ligand with the carbon backbone, SbCSbtBu = 1,3-bis((ditertbutylstibino)methyl)benzene, did not generated any hydrido chloride Ir(III) complex when reacted with [Ir(COE)2Cl]2; however, unidentified insoluble orange solids formed. The SbCSbtBu ligand coordinated with [Cp*IrCl2]2 to afford the piano stool dimer [(Cp*IrCl2)2-μ-SbCSbtBu]. No activity was observed for the hydrido chloride complex bearing the antimony pincer ligand when tested in the transfer dehydrogenation of cyclooctane employing tert-butyl ethene as the acceptor molecule.

Subjects/Keywords: N-Heterocyclic Carbene; Alcohol Oxidation; Microwave; Pincer; Iridium; Antimony

2 more images…

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APA (6^th Edition):

Landers, B. (2017). N-Heterocyclic Carbene- and Antimony Pincer-Transition Metal Complexes: Their Synthesis and Catalytic Activity. (Thesis). University of Hawaii – Manoa. Retrieved from http://hdl.handle.net/10125/51210

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Landers, Brant. “N-Heterocyclic Carbene- and Antimony Pincer-Transition Metal Complexes: Their Synthesis and Catalytic Activity.” 2017. Thesis, University of Hawaii – Manoa. Accessed April 18, 2021. http://hdl.handle.net/10125/51210.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Landers, Brant. “N-Heterocyclic Carbene- and Antimony Pincer-Transition Metal Complexes: Their Synthesis and Catalytic Activity.” 2017. Web. 18 Apr 2021.

Vancouver:

Landers B. N-Heterocyclic Carbene- and Antimony Pincer-Transition Metal Complexes: Their Synthesis and Catalytic Activity. [Internet] [Thesis]. University of Hawaii – Manoa; 2017. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/10125/51210.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Landers B. N-Heterocyclic Carbene- and Antimony Pincer-Transition Metal Complexes: Their Synthesis and Catalytic Activity. [Thesis]. University of Hawaii – Manoa; 2017. Available from: http://hdl.handle.net/10125/51210

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Tennessee – Knoxville

24. Keller, Calvin L. Synthesis of Cationic TetraNHC Complexes of Cobalt, Chromium, Iron, and Platinum for Oxidative Group Transfer.

Degree: 2019, University of Tennessee – Knoxville

URL: https://trace.tennessee.edu/utk_graddiss/5406

► Aziridines are the nitrogen analogue of epoxides, and like epoxides, this functional group is an intermediate in numerous syntheses. Additionally, they are found in several… (more)

▼ Aziridines are the nitrogen analogue of epoxides, and like epoxides, this functional group is an intermediate in numerous syntheses. Additionally, they are found in several natural products with anticancer activity. Despite their chemical applications, aziridine synthesis faces two big challenges: functional group tolerance is limited and a large excess of one reagent is often needed. This research is focused on ameliorating these two limitations.Previous research demonstrated that square planar, strong donor metal complexes, such as porphyrin or macrocyclic tetracarbene complexes were capable of catalyzing aziridination. In our efforts to develop an ideal catalyst for aziridination, we chose to screen a series of transition metals with our tetracarbene ligand to determine which would be most effective for aziridination.A cobalt(II) tetracarbene complex was synthesized by transmetallation and tested for C2 + N1 catalytic aziridination. The complex was unable to catalyze aziridination; furthermore, it showed no reactivity towards organic azides. The oxidative chemistry of the cobalt complex was explored, and a series of cobalt(III) tetracarbene complexes were synthesized. These complexes proved ineffective at aziridination and were unsuitable for further oxidation to a cobalt(IV) complex.A chromium(III) tetracarbene dichloride complex was tested as an aziridination catalyst. The complex proved capable of performing catalytic aziridination at low alkene substrate loadings and performed aziridination with alkenes and azides containing protic functional groups, such as alcohols. The axial chloride ligand on the chromium was proposed as the key to successful catalysis. This complex represents the first ever C2 + N1 aziridination catalyst on a group 6 metal.Following our hypothesis of the penta-coordinated catalyst, an iron(II) pentacarbene complex was synthesized and characterized for aziridination catalysis. While the complex proved an effective catalyst for aziridination at low alkene loadings, the synthesis of the iron complex proved irreproducible.A series of azidoalkenes compounds were synthesized to study the organic chemistry of ring closing intramolecular aziridination. The aziridination reactions had high conversion of the starting materials. However, the reactions proved to be non-catalytic as the control and catalytic yields were identical.

Subjects/Keywords: Catalytic Aziridination; Homogeneous Catalysis; Azide; N-heterocyclic carbene; chromium catalysis

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Keller, C. L. (2019). Synthesis of Cationic TetraNHC Complexes of Cobalt, Chromium, Iron, and Platinum for Oxidative Group Transfer. (Doctoral Dissertation). University of Tennessee – Knoxville. Retrieved from https://trace.tennessee.edu/utk_graddiss/5406

Chicago Manual of Style (16^th Edition):

Keller, Calvin L. “Synthesis of Cationic TetraNHC Complexes of Cobalt, Chromium, Iron, and Platinum for Oxidative Group Transfer.” 2019. Doctoral Dissertation, University of Tennessee – Knoxville. Accessed April 18, 2021. https://trace.tennessee.edu/utk_graddiss/5406.

MLA Handbook (7^th Edition):

Keller, Calvin L. “Synthesis of Cationic TetraNHC Complexes of Cobalt, Chromium, Iron, and Platinum for Oxidative Group Transfer.” 2019. Web. 18 Apr 2021.

Vancouver:

Keller CL. Synthesis of Cationic TetraNHC Complexes of Cobalt, Chromium, Iron, and Platinum for Oxidative Group Transfer. [Internet] [Doctoral dissertation]. University of Tennessee – Knoxville; 2019. [cited 2021 Apr 18]. Available from: https://trace.tennessee.edu/utk_graddiss/5406.

Council of Science Editors:

Keller CL. Synthesis of Cationic TetraNHC Complexes of Cobalt, Chromium, Iron, and Platinum for Oxidative Group Transfer. [Doctoral Dissertation]. University of Tennessee – Knoxville; 2019. Available from: https://trace.tennessee.edu/utk_graddiss/5406

University of New South Wales

25. Buys, Kai. Bis(N-heterocyclic carbene) carbazolide pincer complexes of s- and p-block metals and related studies.

Degree: Chemistry, 2017, University of New South Wales

URL: http://handle.unsw.edu.au/1959.4/57674 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:44496/SOURCE02?view=true

► This work presents synthetic investigations into main group organometallic chemistry, placing particular emphasis on the study of bis N-heterocyclic carbene (NHC) carbazolide coordination environments. Complexes… (more)

▼ This work presents synthetic investigations into main group organometallic chemistry, placing particular emphasis on the study of bis N-heterocyclic carbene (NHC) carbazolide coordination environments. Complexes of high and low oxidation state metals from the s- and p-blocks were targeted and these comprise the content of the experimental chapters two through five.Chapter one serves as a general introduction to rationalise the intent of this work. Herein, focus is drawn to the nascent field of organometallic main group chemistry in the form of a discussion of its history using pertinent recent examples from the literature.Chapter two details the synthesis of an emerging class of versatile bis(NHC)carbazolide pincer ligands; bimcaR, and their complexation to s-block metals. The development of a new zwitterionic bis(imidazolium)carbazolide proligand is discussed, as well as the structural metrics of new lithium and magnesium bimcaR derivatives. Specifically, a new iodomagnesium complex is probed for its synthetic utility as a ligand transfer agent and catalytic precursor in conjunction with attempts to access a reduced Mg(I) derivative.Chapter three focuses on the stabilising effect of the flanking bis(NHC) moieties of bimcaR on high valent group 13 metals and thusly presents a series of exceptionally stable bimcaR supported diiodides from aluminium to thallium. The indium and thallium diiodides are subjected to iodide-hydride exchange reactions to assess the stability of the resulting dihydrides, whilst efforts are also made to access low valent heavy group 13 congeners.Chapter four concentrates on the extension of this methodology to accessing heavy low valent group 14 complexes with the aim of creating highly activated metal centres to harness main group redox chemistry. To this end, a number of attempts are made to access low valent tin and lead halides with a view toward accessing the corresponding, highly reactive metallohydrides. Chapter five presents an alternative approach to accessing such reactive group 14 species with the bulky triazenide ligand class, and thereby details the synthesis and steric characterisation of a new superbulky, unsymmetrical N-2,6-terphenyl triazenide ligand.

Subjects/Keywords: Pincer ligand; Main group organometallic; N-heterocyclic carbene; Carbazolide

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APA (6^th Edition):

Buys, K. (2017). Bis(N-heterocyclic carbene) carbazolide pincer complexes of s- and p-block metals and related studies. (Doctoral Dissertation). University of New South Wales. Retrieved from http://handle.unsw.edu.au/1959.4/57674 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:44496/SOURCE02?view=true

Chicago Manual of Style (16^th Edition):

Buys, Kai. “Bis(N-heterocyclic carbene) carbazolide pincer complexes of s- and p-block metals and related studies.” 2017. Doctoral Dissertation, University of New South Wales. Accessed April 18, 2021. http://handle.unsw.edu.au/1959.4/57674 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:44496/SOURCE02?view=true.

MLA Handbook (7^th Edition):

Buys, Kai. “Bis(N-heterocyclic carbene) carbazolide pincer complexes of s- and p-block metals and related studies.” 2017. Web. 18 Apr 2021.

Vancouver:

Buys K. Bis(N-heterocyclic carbene) carbazolide pincer complexes of s- and p-block metals and related studies. [Internet] [Doctoral dissertation]. University of New South Wales; 2017. [cited 2021 Apr 18]. Available from: http://handle.unsw.edu.au/1959.4/57674 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:44496/SOURCE02?view=true.

Council of Science Editors:

Buys K. Bis(N-heterocyclic carbene) carbazolide pincer complexes of s- and p-block metals and related studies. [Doctoral Dissertation]. University of New South Wales; 2017. Available from: http://handle.unsw.edu.au/1959.4/57674 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:44496/SOURCE02?view=true

University of Texas – Austin

26. Varnado, Charles Daniel, Jr. Design, synthesis, and evaluation of new organometallic and polymeric materials for electrochemical applications.

Degree: PhD, Chemistry, 2013, University of Texas – Austin

URL: http://hdl.handle.net/2152/26876

► The efforts described in this thesis were bifurcated along two distinct projects, but generally were directed toward the development of new materials to solve outstanding… (more)

▼ The efforts described in this thesis were bifurcated along two distinct projects, but generally were directed toward the development of new materials to solve outstanding issues in contemporary electrochemical applications. The first project involved the synthesis and application of redox-switchable olefin metathesis catalysts. N-heterocyclic carbenes (NHCs) bearing ferrocene and other redox-active groups were designed, synthesized, and incorporated into model iridium complexes to evaluate their intrinsic electrochemical and steric parameters. Using these complexes, the ability to switch the electron donating ability of the ligands via redox processes was quantified using a variety of electrochemical and spectroscopic techniques. The donicity was either enhanced or attenutated upon reduction or oxidation of the redox-active group, respectively. The magnitude of the change in donicity upon reduction or oxidation did not vary significantly as a function of the proximity of the redox-active group from the metal center. Thus, other factors, including synthetic considerations, sterics, and redox potential requirements, were determined to guide ligand design. Regardless, redox-active NHCs were adapted into ruthenium-based olefin metathesis catalysts and used to gain control control over various ring-opening metathesis polymerizations and ring-closing metathesis reactions. The second project was focused on the development of new basic polymers for acid/base crosslinked proton exchange membranes intended for applications in direct methanol fuel cells. Polymers containing pendant pyridinyl and pyrimidinyl groups were obtained via the post polymerization functionalization of UDEL® poly(sulfone) and then blended with sulfonated poly(ether ether ketone) (SPEEK). Fuel cells containing these blends were found to exhibit reduced methanol crossover, higher open circuit voltages, and higher maximum power densities compared to plain SPEEK. The differences in fuel cell performance were attributed to the basicity and sterics of the pendant N-heterocycles. Advisors/Committee Members: Bielawski, Christopher W. (advisor).

Subjects/Keywords: N-heterocyclic carbene; Ferrocene; Direct methanol fuel cell

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APA (6^th Edition):

Varnado, Charles Daniel, J. (2013). Design, synthesis, and evaluation of new organometallic and polymeric materials for electrochemical applications. (Doctoral Dissertation). University of Texas – Austin. Retrieved from http://hdl.handle.net/2152/26876

Chicago Manual of Style (16^th Edition):

Varnado, Charles Daniel, Jr. “Design, synthesis, and evaluation of new organometallic and polymeric materials for electrochemical applications.” 2013. Doctoral Dissertation, University of Texas – Austin. Accessed April 18, 2021. http://hdl.handle.net/2152/26876.

MLA Handbook (7^th Edition):

Varnado, Charles Daniel, Jr. “Design, synthesis, and evaluation of new organometallic and polymeric materials for electrochemical applications.” 2013. Web. 18 Apr 2021.

Vancouver:

Varnado, Charles Daniel J. Design, synthesis, and evaluation of new organometallic and polymeric materials for electrochemical applications. [Internet] [Doctoral dissertation]. University of Texas – Austin; 2013. [cited 2021 Apr 18]. Available from: http://hdl.handle.net/2152/26876.

Council of Science Editors:

Varnado, Charles Daniel J. Design, synthesis, and evaluation of new organometallic and polymeric materials for electrochemical applications. [Doctoral Dissertation]. University of Texas – Austin; 2013. Available from: http://hdl.handle.net/2152/26876

University of New South Wales

27. McKay, Alasdair. The synthesis of kinetically stabilised heavy group 13 hydride complexes.

Degree: Chemistry, 2015, University of New South Wales

URL: http://handle.unsw.edu.au/1959.4/55020 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:36374/SOURCE02?view=true

► The work presented in this thesis describes the synthesis and stability of a range of hydrido and low oxidation state complexes of the group 13… (more)

▼ The work presented in this thesis describes the synthesis and stability of a range of hydrido and low oxidation state complexes of the group 13 elements. The underlying theme is the stabilisation of these species. The work upon this subject is divided into eight chapters. Chapter One provides a general introduction to the members of group 13, with particular emphasis on the development of group 13 metal trihydrides and low oxidation group 13 metals. The reasons behind the inherent instability of these species are discussed, and is the development of stabilising ligands.Chapter Two discusses the variability in the stereoelectronic character of stabilising ligands and describes the development of a number of probes to quantify the stereoelectronic character of monoanionic bidentate N,Nʹ-ligands. This Chapter also describes the syntheses of a new super bulky 1,3 bis(2,6 terphenyl)triazene and two C 2,6-terphenyl substituted amidines.Chapter Three introduces the alkali metal chemistry of monoanionic bidentate N,Nʹ ligands. Alkali metal complexes of the aforementioned super bulky ligands (Chapter Two) have been prepared.Chapter Four introduces the +1 oxidation state chemistry of the group 13 metals. The stabilisation of +1 oxidation state group 13 species with triazenide ligands was found to be dependent on the steric character of the ligand employed.Chapter Five introduces the coordination chemistry of trivalent group 13 complexes. The syntheses and crystallographic characterisations of dihalo- and dimethyl group 13 complexes featuring a super bulky triazenide are presented.Chapter Six describes the kinetic stabilisation of group 13 heavy hydrides with monoanionic bidentate N,Nʹ-ligands. The impact of the ligand’s steric character on the thermal stabilities of these complexes is discussed.Chapter Seven introduces the known hydride chemistry of indium and describes the synthesis of a number of NHC adducts of indane (InH3). The decomposition pathways and reactivities of these species were studied.Chapter Eight introduces the stabilisation of low oxidation state main group species by NHCs. A series of dimeric metal dihalide NHC complexes of the form [{MX2(NHC)}2] (M = Ga, In) have been prepared and characterised. Novel bis(NHC) complexes of thallium(I) were also characterised. Advisors/Committee Members: Cole, Marcus, Chemistry, Faculty of Science, UNSW.

Subjects/Keywords: Steric Quantification; Hydride; Group 13; N-Heterocyclic Carbene

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APA (6^th Edition):

McKay, A. (2015). The synthesis of kinetically stabilised heavy group 13 hydride complexes. (Doctoral Dissertation). University of New South Wales. Retrieved from http://handle.unsw.edu.au/1959.4/55020 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:36374/SOURCE02?view=true

Chicago Manual of Style (16^th Edition):

McKay, Alasdair. “The synthesis of kinetically stabilised heavy group 13 hydride complexes.” 2015. Doctoral Dissertation, University of New South Wales. Accessed April 18, 2021. http://handle.unsw.edu.au/1959.4/55020 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:36374/SOURCE02?view=true.

MLA Handbook (7^th Edition):

McKay, Alasdair. “The synthesis of kinetically stabilised heavy group 13 hydride complexes.” 2015. Web. 18 Apr 2021.

Vancouver:

McKay A. The synthesis of kinetically stabilised heavy group 13 hydride complexes. [Internet] [Doctoral dissertation]. University of New South Wales; 2015. [cited 2021 Apr 18]. Available from: http://handle.unsw.edu.au/1959.4/55020 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:36374/SOURCE02?view=true.

Council of Science Editors:

McKay A. The synthesis of kinetically stabilised heavy group 13 hydride complexes. [Doctoral Dissertation]. University of New South Wales; 2015. Available from: http://handle.unsw.edu.au/1959.4/55020 ; https://unsworks.unsw.edu.au/fapi/datastream/unsworks:36374/SOURCE02?view=true

28. Cassirame, Bénédicte. Couplages C-C utilisant des triarylbismuthines catalysés par le PEPPSI : Cross-Coupling Reactions PEPPSI catalysed starting from triarylbismuthines.

Degree: Docteur es, Chimie, 2012, Université Paris-Est

URL: http://www.theses.fr/2012PEST1116

►

Les réactions de couplage métallocatalysées mises en avant par l'attribution du Prix Nobel de Chimie 2010 permettent la création de liaison C-C impossible par les… (more)

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Les réactions de couplage métallocatalysées mises en avant par l'attribution du Prix Nobel de Chimie 2010 permettent la création de liaison C-C impossible par les réactions de type SN1 ou SN2. Or, les composés auxquels elles donnent accès sont très utilisés dans le domaine pharmaceutique, agrochimique ou encore dans celui de la chimie supramoléculaire. Si les réactions sont efficaces, les agents de couplages sont souvent peu accessibles et/ou peu éco(nomique/logique)-compatibles. Les triarylbismuthines lèvent en partie ces limitations, car tous les atomes de ces organométalliques participent aux processus et ces composés sont considérés comme non toxiques mais les réactions engageant ce type d'organométalliques souffrent de leur dimérisation. Afin de lever cette limitation, nous avons développé un système catalytique plus " vert" utilisant le PEPPSI comme pré-catalyseur sur une réaction test. Ces nouvelles conditions donnent généralement d'excellents rendements en série biarylique comme hétérobiarylique. La gamme des substituants sur le dérivé halogéné est très étendue mais plus limitée sur la bismuthine. Ce système catalytique a ensuite été utilisé sans modification dans les réactions domino d'élimination/couplage. Une étude cinétique comparative par GC/MS et RMN 13C a permis de montrer qu'une élimination d'ordre 2 avait lieu avant le couplage. De plus il y a un effet coopératif entre les ions fluorures et la bismuthine : celle-ci joue donc un double rôle : agent organométallique doux de couplage et base. L'ambiguïté mécanistique ainsi levée, il a été permis d'envisager une chimiosélectivité en fonction des divers états d'hybridation du carbone portant le brome au moment du couplage. Plusieurs méthodes d'accès à des molécules de structures Ar-Ar-C C-Ar à géométries variables peuvent être obtenues rapidement. Le système catalytique a également permet l'activation de liaison C-Br de bromocoumarines. Ainsi, il est possible de réaliser le couplage sur les positions 3-, 4- et 6-. L'ordre de réactivité a été déterminé ce qui a permis de réaliser des monocouplages parfaitement sélectifs sur les 3,4- ou 3,6- dibromocoumarines, dont les applications biologiques suscitent un grand intérêt. Le nouveau système catalytique a donc éliminé le problème de dimérisation des triarylbismuthines et donne potentiellement accès à des molécules intéressantes pour leurs propriétés physiques ou biologiques

Metallocatalysed crosscoupling reactions have been highlighted by the attribution of the 2010 Nobel Chemistry Price since they allow CC bond formation when classical SN1 or SN2 do not permit it. Furthermore, they give access to many pharmaceutics and agronomic compounds but also molecules used for their supramolecular properties. Nowadays, reactions are really efficient but reactants are not always readily accessible and can't be classified as green reagents. Since all its atoms act over the catalytic process and because they are not considered as toxic so far, triarylbismuthines may be a good alternative to circumvent the limitation…

Advisors/Committee Members: Condon, Sylvie (thesis director).

Subjects/Keywords: Catalyse; Triarylbismuthines; Carbène N-hétérocyclique; PEPPSI; Catalysis; Triarylbismuthines; N-heterocyclic carbene; PEPPSI

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APA (6^th Edition):

Cassirame, B. (2012). Couplages C-C utilisant des triarylbismuthines catalysés par le PEPPSI : Cross-Coupling Reactions PEPPSI catalysed starting from triarylbismuthines. (Doctoral Dissertation). Université Paris-Est. Retrieved from http://www.theses.fr/2012PEST1116

Chicago Manual of Style (16^th Edition):

Cassirame, Bénédicte. “Couplages C-C utilisant des triarylbismuthines catalysés par le PEPPSI : Cross-Coupling Reactions PEPPSI catalysed starting from triarylbismuthines.” 2012. Doctoral Dissertation, Université Paris-Est. Accessed April 18, 2021. http://www.theses.fr/2012PEST1116.

MLA Handbook (7^th Edition):

Cassirame, Bénédicte. “Couplages C-C utilisant des triarylbismuthines catalysés par le PEPPSI : Cross-Coupling Reactions PEPPSI catalysed starting from triarylbismuthines.” 2012. Web. 18 Apr 2021.

Vancouver:

Cassirame B. Couplages C-C utilisant des triarylbismuthines catalysés par le PEPPSI : Cross-Coupling Reactions PEPPSI catalysed starting from triarylbismuthines. [Internet] [Doctoral dissertation]. Université Paris-Est; 2012. [cited 2021 Apr 18]. Available from: http://www.theses.fr/2012PEST1116.

Council of Science Editors:

Cassirame B. Couplages C-C utilisant des triarylbismuthines catalysés par le PEPPSI : Cross-Coupling Reactions PEPPSI catalysed starting from triarylbismuthines. [Doctoral Dissertation]. Université Paris-Est; 2012. Available from: http://www.theses.fr/2012PEST1116

29. Ling, Xiang. N-heterocyclic carbenes coated nanocrystals and supracrystals : Nanocristaux habillés par des carbènes N-hétérocycliques et supracristaux.

Degree: Docteur es, Chimie Physique, 2015, Université Pierre et Marie Curie – Paris VI

URL: http://www.theses.fr/2015PA066334

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Les nanomatériaux ont beaucoup captivé l'attention pour leur propriétés uniques, fortement associées à leurs dimensions nanoscopiques. En particulier, les nanoparticules (NP) à base de métaux… (more)

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Les nanomatériaux ont beaucoup captivé l'attention pour leur propriétés uniques, fortement associées à leurs dimensions nanoscopiques. En particulier, les nanoparticules (NP) à base de métaux nobles (Au, Ag) présentent des propriétés mécaniques, électroniques, optiques et magnétiques particulières intéressantes pour le développement d'applications dans de nombreux domaines à fort impact sociétal. En raison de leur stabilité élevée par rapport aux autres nano- particules métalliques, les nanoparticules d'or ont été abondamment explorées pour les nanotechnologies. Ces dernières décennies, les NHC ont émergé en tant que classe essentielle de ligands neutres en chimie organométallique. Les NHC sont caractérisés par leur flexibilité synthétique élevée, leur géométrie spécifique, et une liaison métal–Ccarbène très forte dans les complexes métalliques. Toutes ces propriétés ont été largement étudiées et exploitées pour les applications en catalyse homogène et pour le développement de complexes biologiquement actifs. Par comparaison, l'utilisation des NHC dans les matériaux reste largement peu explorée. Dans ce travail, le potentiel de ligands NHC dans le domaine des nanomatériaux, comme des agents de revêtement pour le produit nanocristaux de synthèse de l'or (et l'argent), la produit de stabilisation et de l'auto-assemblage dans supracrystals ont été explorés. Tout d'abord, des complexes d'argent et d'or-NHC qui sont bien définies avec différents ligands qui sont connus comme le NHC, sont étudiés pour leur pertinence afin de générer des astable nanocristaux (NCs) dans des conditions réductrices avec un bon contrôle de la taille des nanocristaux. Nous démontrons que le Au et le Ag NCs peuvent tous être formés par la réduction des complexes métal-NHC avec les amine-boranes. L'efficacité du procédé, la taille moyenne et la taille de la répartition des nanocristaux dépendent fortement de la structure du ligand NHC. Cependant, nous démontrons dans cette partie que les différentes voies sont impliqués à générer des nanocristaux par Au ou Ag précurseurs, comme une spécifique réaction observée entre Ag-NHC et thiols conduisant à la formation de thiolates argent alors que le Au-NHC correspondant reste inchangé...

Nanomaterials have received extraordinary attention owing to their unique properties, strongly associated to their nanoscale dimensions. In particular, noble metal (Au, Ag) nanoparticles (NPs) exhibit particular mechanical, electronic, optical and magnetic properties and present a high potential for developing applications in many domains with important societal impacts. Due to their higher stability by comparison with other metal-based nanoparticles, Au NPs have been extensively investigated for research in nanotechnology. In the last decades, N-Heterocyclic carbenes (NHCs) have emerged as an essential class of neutral ligands in organometallic chemistry. NHCs are characterized by their high synthetic flexibility, their specific geometry, and a very strong metalCcarbene bond in metal complexes. All these properties…

Advisors/Committee Members: Pileni, Marie Paule (thesis director).

Subjects/Keywords: Or; Carbène N-Hétérocyclique; Nanocristal; Auto-Assemblage; Supracrystal; Stabilité; Gold; N-Heterocyclic carbene; 541.3

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Ling, X. (2015). N-heterocyclic carbenes coated nanocrystals and supracrystals : Nanocristaux habillés par des carbènes N-hétérocycliques et supracristaux. (Doctoral Dissertation). Université Pierre et Marie Curie – Paris VI. Retrieved from http://www.theses.fr/2015PA066334

Chicago Manual of Style (16^th Edition):

Ling, Xiang. “N-heterocyclic carbenes coated nanocrystals and supracrystals : Nanocristaux habillés par des carbènes N-hétérocycliques et supracristaux.” 2015. Doctoral Dissertation, Université Pierre et Marie Curie – Paris VI. Accessed April 18, 2021. http://www.theses.fr/2015PA066334.

MLA Handbook (7^th Edition):

Ling, Xiang. “N-heterocyclic carbenes coated nanocrystals and supracrystals : Nanocristaux habillés par des carbènes N-hétérocycliques et supracristaux.” 2015. Web. 18 Apr 2021.

Vancouver:

Ling X. N-heterocyclic carbenes coated nanocrystals and supracrystals : Nanocristaux habillés par des carbènes N-hétérocycliques et supracristaux. [Internet] [Doctoral dissertation]. Université Pierre et Marie Curie – Paris VI; 2015. [cited 2021 Apr 18]. Available from: http://www.theses.fr/2015PA066334.

Council of Science Editors:

Ling X. N-heterocyclic carbenes coated nanocrystals and supracrystals : Nanocristaux habillés par des carbènes N-hétérocycliques et supracristaux. [Doctoral Dissertation]. Université Pierre et Marie Curie – Paris VI; 2015. Available from: http://www.theses.fr/2015PA066334

30. Zhang, Pinglu. Cyclodextrin-(N-Heterocyclic Carbene)-Metal Complexes for Cavity-Dependent Catalysis : Des complexes de cyclodextrine-(Carbène N-Hétérocycliques)-métaux pour catalyse dépendante de la cavité.

Degree: Docteur es, Chimie Organique, 2015, Université Pierre et Marie Curie – Paris VI

URL: http://www.theses.fr/2015PA066380

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Des complexes de Cyclodextrine (CD)-NHC-Métaux (NHC= Carbènes N-Hétérocycliques), comprenant des métaux tel que AgI, CuI et AuI ont été synthétisés. Une étude structurale a mis… (more)

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Des complexes de Cyclodextrine (CD)-NHC-Métaux (NHC= Carbènes N-Hétérocycliques), comprenant des métaux tel que AgI, CuI et AuI ont été synthétisés. Une étude structurale a mis en évidence la position intra-cavitaire du métal, induisant des interactions C-H…M, C-H…X et π…X. L’influence du type de cavité (α-, β-, γ-CD) et du type de dérivés NHC (Imidazole, benzimidazole, triazole) a été étudiée. Les interactions diminuent avec l’augmentation de la taille de la cavité et en parallèle, celles-ci ont été amplifiées avec des dérivés NHC possédant un effet donneur plus fort. Les complexes de cuivre correspondants montrent une bonne réactivité pour la réaction d’hydroboration des alcynes. Il a de plus été observé que la sélectivité est dépendante de la taille de la cavité. En effet, alors que le complexe α-CD-Cu donne le produit linéaire, le complexe β-CD-Cu oriente vers la formation de l’isomère branché. Les espèces CD-Cu potentiellement impliquées dans le cycle catalytique ont été étudiées. Deux mécanismes différents sont ainsi proposés. Dans la réaction catalysée par le complexe α-CD-Cu, le processus catalytique a lieu en dehors de la cavité; tandis que lorsque la cavité est plus grande (β-CD) la catalyse a lieu à l’intérieur de la celle-ci. Par ailleurs, les complexes ont également montré une différente énantiosélectivité et régiosélectivité dans une réaction de cycloisomerization catalysée par des comlexes dor, en fonction de la taille de la cavité de ces catalyseurs. Les résultats catalytiques ont prouvé que les complexes CD-NHC-Métaux fonctionnent comme des catalyseurs pour lesquels la taille de la cavité influe sur la séléctivité.

Cyclodextrin (CD)-NHC-Metal complexes (NHC=N-Heterocyclic Carbene), including the AgI, CuI and AuI complexes were synthesized. A structural study showed that the metal was inside the cavity, and induced by C-H…M, C-H…X and π…X interactions. Variations on α-, β-, γ-CD cavities and NHC derivatives (midazole, benzimidazole, triazole) were studied. When the size of the cavity increased, these interactions decreased. Furthermore, stronger σ-donating effects lead to stronger interactions. CD-Cu complexes showed good activity in catalytic hydroboration of alkynes. The selectivity is depending on the size of the cavity of the catalyst. α-CD copper complex gives linear hydroboration products, while β-CD copper complex yields the branched isomers. The CD-Cu species potentially involved in the catalytic cycle were studied, two different mechanisms were thus proposed. In the α-CD-Cu complex catalyzed reactions, the catalytic process takes place outside the cavity; while a bigger cavity β-CD permits the catalysis to take place inside the cavity. Furthermore, the gold complexes also show different enantioselectivity and regioselectivity in cycloisomerization using different cavity-based catalysts. Catalytic results evidenced the selectivity of a catalytic reaction is dependent on the cavity of the CD-NHC-metal complexes.

Advisors/Committee Members: Sollogoub, Matthieu (thesis director), Roland, Sylvain (thesis director), Zhang, Yongmin (thesis director).

Subjects/Keywords: Cyclodextrines; Carbènes N-Hétérocycliques; Organométalliques; Carbènes Mésoionique; Catalyseur; Cyclodextrins; N-Heterocyclic Carbene; Organometallics; 540

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Zhang, P. (2015). Cyclodextrin-(N-Heterocyclic Carbene)-Metal Complexes for Cavity-Dependent Catalysis : Des complexes de cyclodextrine-(Carbène N-Hétérocycliques)-métaux pour catalyse dépendante de la cavité. (Doctoral Dissertation). Université Pierre et Marie Curie – Paris VI. Retrieved from http://www.theses.fr/2015PA066380

Chicago Manual of Style (16^th Edition):

Zhang, Pinglu. “Cyclodextrin-(N-Heterocyclic Carbene)-Metal Complexes for Cavity-Dependent Catalysis : Des complexes de cyclodextrine-(Carbène N-Hétérocycliques)-métaux pour catalyse dépendante de la cavité.” 2015. Doctoral Dissertation, Université Pierre et Marie Curie – Paris VI. Accessed April 18, 2021. http://www.theses.fr/2015PA066380.

MLA Handbook (7^th Edition):

Zhang, Pinglu. “Cyclodextrin-(N-Heterocyclic Carbene)-Metal Complexes for Cavity-Dependent Catalysis : Des complexes de cyclodextrine-(Carbène N-Hétérocycliques)-métaux pour catalyse dépendante de la cavité.” 2015. Web. 18 Apr 2021.

Vancouver:

Zhang P. Cyclodextrin-(N-Heterocyclic Carbene)-Metal Complexes for Cavity-Dependent Catalysis : Des complexes de cyclodextrine-(Carbène N-Hétérocycliques)-métaux pour catalyse dépendante de la cavité. [Internet] [Doctoral dissertation]. Université Pierre et Marie Curie – Paris VI; 2015. [cited 2021 Apr 18]. Available from: http://www.theses.fr/2015PA066380.

Council of Science Editors:

Zhang P. Cyclodextrin-(N-Heterocyclic Carbene)-Metal Complexes for Cavity-Dependent Catalysis : Des complexes de cyclodextrine-(Carbène N-Hétérocycliques)-métaux pour catalyse dépendante de la cavité. [Doctoral Dissertation]. Université Pierre et Marie Curie – Paris VI; 2015. Available from: http://www.theses.fr/2015PA066380

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