Discovery and Development of New Metal Catalyzed Methods to Key Building Blocks in Organic Synthesis

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dc.contributor.advisorFrantz, Doug E.
dc.contributor.authorMunteanu, Charissa
dc.contributor.committeeMemberDoyle, Michael P.
dc.contributor.committeeMemberLarionov, Oleg V.
dc.contributor.committeeMemberMcHardy, Stanton F.
dc.contributor.committeeMemberTonzetich, Zachary J.
dc.date.accessioned2024-02-12T18:30:21Z
dc.date.available2020-06-16
dc.date.available2024-02-12T18:30:21Z
dc.date.issued2019
dc.descriptionThis item is available only to currently enrolled UTSA students, faculty or staff. To download, navigate to Log In in the top right-hand corner of this screen, then select Log in with my UTSA ID.
dc.description.abstractThis dissertation will provide the details of metal-catalyzed transformations to key building blocks in organic synthesis. In particular the synthesis of alkynes, allenes and aryl boronic acids will be described. The first transformation was achieved through a catalytic decarboxylation/elimination of (E)-enol triflates bearing an allylic ester to obtain alkynes via palladium catalysis. This methodology allows for a general, mild and robust synthesis of three different alkynes including internal, terminal and halogenated alkynes. The second transformation demonstrates the use of alkynes and aryl chlorides in the presence of a palladium catalyst to synthesize tri-substituted allenes. This process takes advantage of a vinyl-Pd(II) species which can undergo a β-hydride elimination to access the desired allene. Lastly, borylation reactions of aryl halides and pseudo aryl halides utilizing both palladium and nickel catalysis will be described. This process highlights the importance of halide sequestering during the course of the borylation reaction resulting in catalyst loadings as low as 0.01 mol %. Furthermore, the utility of the borylation transformation will be demonstrated through late-stage functionalization and tandem/telescoping reactions.
dc.description.departmentChemistry
dc.format.extent288 pages
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/20.500.12588/4820
dc.languageen
dc.subjectalkyne
dc.subjectallene
dc.subjectMetal catalyzed borylation
dc.subjectSuzuki cross-coupling
dc.subject.classificationChemistry
dc.subject.classificationOrganic chemistry
dc.titleDiscovery and Development of New Metal Catalyzed Methods to Key Building Blocks in Organic Synthesis
dc.typeThesis
dc.type.dcmiText
dcterms.accessRightspq_closed
thesis.degree.departmentChemistry
thesis.degree.grantorUniversity of Texas at San Antonio
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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