Daugulis, Olafs2021-08-06December 22020-12December 2Portions of this document appear in: Aderibigbe, Sabrina O., and Don M. Coltart. "Synthesis of 1, 3-Diketones and β-Keto Thioesters via Soft Enolization." The Journal of organic chemistry 84, no. 15 (2019): 9770-9777.https://hdl.handle.net/10657/8023Synthetic methodology development towards convenient C-C bond and C-F bond formation is a desirable synthetic tool for industry and academia. Using commercially available substrates towards chemical transformations is often a strategy used to simplify the process of synthesizing compounds. This dissertation focuses on the synthetic methodology development of C-C and C-F bond formation for broad applicational utility. This dissertation will discuss two synthetic strategies towards C-C bond formation, soft enolization and Umpolung-like chemistry. The direct synthesis of 1,3-diketones and β-keto thioesters using in good yields and with wide substrate tolerance was possible using our soft enolization strategy using crude acyl chlorides. Another C-C bond strategy explored was an Umpolung-like approach towards α-functionalization of ketones. Ketones are synthetically important functional group and have wide applicational uses within chemistry and biology. The α-functionalization of ketones and their derivatives via addition of their corresponding (aza) enolates to alkyl halides is a fundamental synthetic transformation but has been historically less explored despite its potential widespread utility. Our approach towards uses a novel β-silylated azoalkenes intermediate towards anti-diastereoselective α-alkylation of ketones. In addition, we explored a streamlined approach towards monofluorohydrocarbon formation via electrophilic fluorination of organozinc compounds. We hope this will have wide applicational utility as C-F bonds are important within agrochemistry and pharmaceutical chemistry.application/pdfengThe author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. UH Libraries has secured permission to reproduce any and all previously published materials contained in the work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).monofluorinationsoft enolizationphenyl azoalkeneUmpolung-like chemistryorganozinccarbon-carbon bond formationdiastereoselective2021-08-06Thesisborn digital