1. C-C Bond Formation via Soft Enolization and Umpolung-like Chemistry 2. Electrophilic Fluorination of Organozinc Reagents



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Synthetic 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.



monofluorination, soft enolization, phenyl azoalkene, Umpolung-like chemistry, organozinc, carbon-carbon bond formation, diastereoselective


Portions 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.