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University of California – San Diego

1. Lee, SangHyun. Palladium-catalyzed decarbonylative cross-coupling of cinnamic esters with silicon-based nucleophiles/enolates and oxidative decarboxylative cross-coupling of cinnamic acids with enolate precursors.

Degree: Chemistry, 2018, University of California – San Diego

Transition metal-catalyzed cross-coupling is a powerful methodology to strategically form carbon-carbon or carbon-heteroatom bonds. Advancements in cross-coupling strategies with diverse organometallic nucleophile reagents have been well recognized, however, developments that expand the scope of viable electrophilic partners have only recently been invigorated. Of particular interest is the development of new coupling strategies where both the nucleophilic and electrophilic coupling partner could be derived from oxygenated precursors rather than halogenated precursors, which is the current standard. This thesis describes efforts toward the development of new synthetic methodologies to achieve a-vinylation of enolizable carbonyls in two parts: 1) Pd-catalyzed decarbonylative Hiyama-type cross-coupling of cinnamate esters and aryl silanes and 2) radical-mediated oxidative decarboxylative coupling of cinnamic acids and simple ketones.

Subjects/Keywords: Chemistry; cross-coupling; decarbonylative coupling; decarboxylative coupling; Hiyama-type; oxygenated precursors; radical-mediated coupling

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

APA (6th Edition):

Lee, S. (2018). Palladium-catalyzed decarbonylative cross-coupling of cinnamic esters with silicon-based nucleophiles/enolates and oxidative decarboxylative cross-coupling of cinnamic acids with enolate precursors. (Thesis). University of California – San Diego. Retrieved from http://www.escholarship.org/uc/item/5s81c8m1

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):

Lee, SangHyun. “Palladium-catalyzed decarbonylative cross-coupling of cinnamic esters with silicon-based nucleophiles/enolates and oxidative decarboxylative cross-coupling of cinnamic acids with enolate precursors.” 2018. Thesis, University of California – San Diego. Accessed March 21, 2019. http://www.escholarship.org/uc/item/5s81c8m1.

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

MLA Handbook (7th Edition):

Lee, SangHyun. “Palladium-catalyzed decarbonylative cross-coupling of cinnamic esters with silicon-based nucleophiles/enolates and oxidative decarboxylative cross-coupling of cinnamic acids with enolate precursors.” 2018. Web. 21 Mar 2019.

Vancouver:

Lee S. Palladium-catalyzed decarbonylative cross-coupling of cinnamic esters with silicon-based nucleophiles/enolates and oxidative decarboxylative cross-coupling of cinnamic acids with enolate precursors. [Internet] [Thesis]. University of California – San Diego; 2018. [cited 2019 Mar 21]. Available from: http://www.escholarship.org/uc/item/5s81c8m1.

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

Council of Science Editors:

Lee S. Palladium-catalyzed decarbonylative cross-coupling of cinnamic esters with silicon-based nucleophiles/enolates and oxidative decarboxylative cross-coupling of cinnamic acids with enolate precursors. [Thesis]. University of California – San Diego; 2018. Available from: http://www.escholarship.org/uc/item/5s81c8m1

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

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