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

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dc.contributor.advisorDaugulis, Olafs
dc.contributor.committeeMemberMay, Jeremy A.
dc.contributor.committeeMemberGilbertson, Scott R.
dc.contributor.committeeMemberChen, Tai-Yen
dc.contributor.committeeMemberOzerov, Oleg V.
dc.creatorAderibigbe, Sabrina Olunike Wande
dc.date.accessioned2021-08-06T19:14:49Z
dc.date.createdDecember 2020
dc.date.issued2020-12
dc.date.submittedDecember 2020
dc.date.updated2021-08-06T19:14:50Z
dc.description.abstractSynthetic 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.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginborn digital
dc.format.mimetypeapplication/pdf
dc.identifier.citationPortions 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.
dc.identifier.urihttps://hdl.handle.net/10657/8023
dc.language.isoeng
dc.rightsThe 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).
dc.subjectmonofluorination
dc.subjectsoft enolization
dc.subjectphenyl azoalkene
dc.subjectUmpolung-like chemistry
dc.subjectorganozinc
dc.subjectcarbon-carbon bond formation
dc.subjectdiastereoselective
dc.title1. C-C Bond Formation via Soft Enolization and Umpolung-like Chemistry 2. Electrophilic Fluorination of Organozinc Reagents
dc.type.dcmiText
dc.type.genreThesis
local.embargo.lift2022-12-01
local.embargo.terms2022-12-01
thesis.degree.collegeCollege of Natural Sciences and Mathematics
thesis.degree.departmentChemistry, Department of
thesis.degree.disciplineChemistry
thesis.degree.grantorUniversity of Houston
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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