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Universitat Rovira i Virgili

1. Ziadi, Asraa. Metal-catalyzed functionalization of c-c bonds in four-membered rings.

Degree: Departament de Química Analítica i Química Orgànica, 2014, Universitat Rovira i Virgili

The means to promote catalytic C-C bond-functionalization has gained a considerable attention in recent years and probably can be considered one of the most challenging and vibrant subjects in organometallic chemistry. This PhD thesis deals with the design of new metal-catalyzed functionalization of C-C bonds in four-membered ring frameworks. Specifically, we have demonstrated the viability of preparing γ-arylated ketones via Pd-catalyzed cleavage of C-C bonds in tert-cyclobutanol using aryl chloride or tosylate counterparts (Chapter 2). The transformation possesses a wide substrate scope and remarkable low catalyst loadings. Selectivity was controlled by the ligand in which electron-rich and sterically-hindered phosphine ligands provided a unique reaction outcome that avoided the proclivity of alkyl metal species towards destructive β−hydride elimination. Prompted by the precedents in Chapter 2, we successfully extended the scope of the metal-catalyzed C-C bond-cleavage of tert-cyclobutanols by using halo acetylene counterparts giving γ-alkynylated ketones (Chapter 3). Interestingly, substituents on the alkyne motif showed a remarkable influence on reactivity. Of particular interest is the application profile of such methodology since γ-alkynylated ketones could promote consecutive metal-catalyzed transformations into valuable synthetic intermediates. In Chapter 4, we extended the interest for C-C bond-cleavage beyond the use of tert-cycñobutanols. Specifically, we developed a Ni-catalyzed C-C bond-cleavage event in benzocyclobutenones for preparing eight-membered rings via formal [4+4]-cycloaddition with dienes (Chapter 4). The method shows a specific preference for eight-membered rings over thermodynamically more stable six-membered rings. This PhD thesis has also studied the development of catalytic CO2 fixation and C-F bond-formation via C-C bond-cleavage (Chapter 5). While we have not found reaction conditions to effect the desired transformations, our research group is actively involved in related catalytic endeavors and it is expected that such research will shed light into the targeted CO2 fixation or C-F bond-forming reactions via C-C bond-cleavage. Advisors/Committee Members: [email protected] (authoremail), false (authoremailshow), Martín Romo, Rubén (director), true (authorsendemail).

Subjects/Keywords: química organometàlica; functionalització C-C; catalitzada; Activación de enlaces C-C; Paladio; Catálisis; C-C bond cleavage; Palladium; Catalysis; 54; 542; 546; 547

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

APA (6th Edition):

Ziadi, A. (2014). Metal-catalyzed functionalization of c-c bonds in four-membered rings. (Thesis). Universitat Rovira i Virgili. Retrieved from http://hdl.handle.net/10803/320185

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

Chicago Manual of Style (16th Edition):

Ziadi, Asraa. “Metal-catalyzed functionalization of c-c bonds in four-membered rings.” 2014. Thesis, Universitat Rovira i Virgili. Accessed October 15, 2019. http://hdl.handle.net/10803/320185.

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

MLA Handbook (7th Edition):

Ziadi, Asraa. “Metal-catalyzed functionalization of c-c bonds in four-membered rings.” 2014. Web. 15 Oct 2019.

Vancouver:

Ziadi A. Metal-catalyzed functionalization of c-c bonds in four-membered rings. [Internet] [Thesis]. Universitat Rovira i Virgili; 2014. [cited 2019 Oct 15]. Available from: http://hdl.handle.net/10803/320185.

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

Council of Science Editors:

Ziadi A. Metal-catalyzed functionalization of c-c bonds in four-membered rings. [Thesis]. Universitat Rovira i Virgili; 2014. Available from: http://hdl.handle.net/10803/320185

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

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