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You searched for +publisher:"Colorado State University" +contributor:("McNally, Andrew"). Showing records 1 – 3 of 3 total matches.

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Colorado State University

1. Ozboya, Kerem. Development of an asymmetric NHC-catalyzed cascade reaction and studies towards the asymmetric aminomethylation of enals.

Degree: PhD, Chemistry, 2015, Colorado State University

A cascade reaction is developed to form complex cyclopentanones using an asymmetric Michael/Benzoin sequence. This reaction employs simple aliphatic aldehydes and ketoesters in conjunction with a chiral amine catalyst and a chiral NHC catalyst. Further investigation reveals a surprising interplay between these two catalysts. This relationship is manifested in a pseudo-dynamic kinetic resolution, which is responsible for the high diastereoselectivity observed. Subsequent work details the discovery of the aminomethylation of enals using NHC catalysis. This reaction utilizes an iminium source as well as cinnamaldehyde derivatives to form gamma-amino butyrate derivatives. Rendering this reaction asymmetric has proven a challenge, despite extensive effort to resolve these issues. In the course of these studies, an unexpected NHC-catalyzed Morita-Baylis-Hillman reaction was observed. Optimal conditions for this reaction were established, proving access to useful amino-enals. In an effort to design suitable catalysts for the asymmetric aminomethylation reaction, a strategy for the late-stage manipulation of NHC catalysts was developed. Key to this strategy is the `protection' of the triazolium salt by reduction to the triazoline. An aryl C-Br bond is then exploited for cross-coupling reactions, building a small library of new catalysts. The triazolium salt is then recovered by oxidation with a trityl salt. Advisors/Committee Members: Rovis, Tomislav (advisor), Henry, Charles (committee member), McNally, Andrew (committee member), Kennan, Alan (committee member), Inamine, Julia (committee member).

Subjects/Keywords: NHC; Organocatalysis; Organic Synthesis; Asymmetric Catalysis

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APA (6th Edition):

Ozboya, K. (2015). Development of an asymmetric NHC-catalyzed cascade reaction and studies towards the asymmetric aminomethylation of enals. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/166865

Chicago Manual of Style (16th Edition):

Ozboya, Kerem. “Development of an asymmetric NHC-catalyzed cascade reaction and studies towards the asymmetric aminomethylation of enals.” 2015. Doctoral Dissertation, Colorado State University. Accessed January 21, 2018. http://hdl.handle.net/10217/166865.

MLA Handbook (7th Edition):

Ozboya, Kerem. “Development of an asymmetric NHC-catalyzed cascade reaction and studies towards the asymmetric aminomethylation of enals.” 2015. Web. 21 Jan 2018.

Vancouver:

Ozboya K. Development of an asymmetric NHC-catalyzed cascade reaction and studies towards the asymmetric aminomethylation of enals. [Internet] [Doctoral dissertation]. Colorado State University; 2015. [cited 2018 Jan 21]. Available from: http://hdl.handle.net/10217/166865.

Council of Science Editors:

Ozboya K. Development of an asymmetric NHC-catalyzed cascade reaction and studies towards the asymmetric aminomethylation of enals. [Doctoral Dissertation]. Colorado State University; 2015. Available from: http://hdl.handle.net/10217/166865

2. Ruhl, Kyle E. The development and applications of light-gated cobalt catalysis.

Degree: PhD, Chemistry, 2017, Colorado State University

Transition metals are an important natural resource and an essential component of many industrial processes and applications. Examples of these include air-quality control, electronics manufacture, agriculture, pharmaceuticals, and petro-chemistry. Within the field of synthetic chemistry, transition metal catalysts minimize waste, decrease expense, and enable rapid construction of small molecules. Over the past decade, transition-metal-based polypyridyl complexes have been the cornerstone of photo-redox catalysis which facilitate electron transfer and allow synthetic chemists to functionalize inert functionalities using visible-light energy. The first chapter of this work introduces rhodium- and cobalt-catalyzed [2+2+2] cycloadditions as well as photo-redox catalysis. The following chapter covers our group's progress toward the merger of photo-redox and cobalt catalysis as well as the multi-disciplinary approach we have used to understand mechanism. The third chapter explores light-gated catalysis and its importance for spatially and temporally resolved methods. Finally, the fourth chapter focuses on the applications of light-gated cobalt catalysis. We have found a light-gated cobalt catalyst to temporally control the [2+2+2] cycloaddition, and when combined with photolithography, enable a spatially resolved method for arene formation. Advisors/Committee Members: Rovis, Tomislav (advisor), McNally, Andrew (committee member), Neilson, James R. (committee member), Kipper, Matthew J. (committee member).

Subjects/Keywords: Cobalt; Light; Catalysis; Photoredox; Gated

…experimentation platform at Colorado State University, the 20 initial experiment included six cobalt… 

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

APA (6th Edition):

Ruhl, K. E. (2017). The development and applications of light-gated cobalt catalysis. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/181308

Chicago Manual of Style (16th Edition):

Ruhl, Kyle E. “The development and applications of light-gated cobalt catalysis.” 2017. Doctoral Dissertation, Colorado State University. Accessed January 21, 2018. http://hdl.handle.net/10217/181308.

MLA Handbook (7th Edition):

Ruhl, Kyle E. “The development and applications of light-gated cobalt catalysis.” 2017. Web. 21 Jan 2018.

Vancouver:

Ruhl KE. The development and applications of light-gated cobalt catalysis. [Internet] [Doctoral dissertation]. Colorado State University; 2017. [cited 2018 Jan 21]. Available from: http://hdl.handle.net/10217/181308.

Council of Science Editors:

Ruhl KE. The development and applications of light-gated cobalt catalysis. [Doctoral Dissertation]. Colorado State University; 2017. Available from: http://hdl.handle.net/10217/181308


Colorado State University

3. Neely, Jamie M. Reaction development and mechanistic investigation of rhodium-catalyzed pyridine synthesis via C-H activation.

Degree: PhD, Chemistry, 2007, Colorado State University

Described herein are two complementary rhodium-catalyzed methods for the synthesis of substituted pyridines from unsaturated oxime derivatives and alkenes. In the first, formal [4+2] cycloaddition of O-pivaloyl α, β-unsaturated oxime esters and activated terminal alkenes was discovered to proceed in high yields and with excellent selectivity for 6-substituted pyridine products. Mechanistic experiments were found to be consistent with a reversible C-H activation step and a C-N bond forming, N-O bond cleaving process en route to pyridine formation. Rhodium-catalyzed coupling using unactivated alkene substrates was shown to present important information regarding the influence of the alkene component on product distribution. In a second method, access to 5-substituted pyridine derivatives was achieved by decarboxylative annulation of α, β-unsaturated oxime esters and β-substituted acrylic acid derivatives. In this case, carboxylic acids were found to serve as traceless activating groups for selective alkene incorporation. A wealth of mechanistic insight was gained by identification of and decomposition studies regarding catalytically relevant rhodium complexes. Advisors/Committee Members: Rovis, Tomislav (advisor), McNally, Andrew (committee member), Fisk, John D. (committee member), Neilson, James R. (committee member), Inamine, Julia M. (committee member).

Subjects/Keywords: rhodium; oxime esters; pyridines; alkenes; C-H activation

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

APA (6th Edition):

Neely, J. M. (2007). Reaction development and mechanistic investigation of rhodium-catalyzed pyridine synthesis via C-H activation. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/88453

Chicago Manual of Style (16th Edition):

Neely, Jamie M. “Reaction development and mechanistic investigation of rhodium-catalyzed pyridine synthesis via C-H activation.” 2007. Doctoral Dissertation, Colorado State University. Accessed January 21, 2018. http://hdl.handle.net/10217/88453.

MLA Handbook (7th Edition):

Neely, Jamie M. “Reaction development and mechanistic investigation of rhodium-catalyzed pyridine synthesis via C-H activation.” 2007. Web. 21 Jan 2018.

Vancouver:

Neely JM. Reaction development and mechanistic investigation of rhodium-catalyzed pyridine synthesis via C-H activation. [Internet] [Doctoral dissertation]. Colorado State University; 2007. [cited 2018 Jan 21]. Available from: http://hdl.handle.net/10217/88453.

Council of Science Editors:

Neely JM. Reaction development and mechanistic investigation of rhodium-catalyzed pyridine synthesis via C-H activation. [Doctoral Dissertation]. Colorado State University; 2007. Available from: http://hdl.handle.net/10217/88453

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