N-alkynylations of substituted pyrroles with 1-bromo-1-alkynes and C-alkylations and C-alkenylations of cyclic 1,2-diketones

dc.contributor.advisorMartin, Stephen F.
dc.contributor.advisorKerwin, Sean M.
dc.contributor.committeeMemberAnslyn, Eric
dc.contributor.committeeMemberBrodbelt, Jennifer
dc.contributor.committeeMemberLiu, Hung-Wen
dc.contributor.committeeMemberDong, Guangbin
dc.creatorReinus, Brandon Joseph
dc.date.accessioned2019-09-17T15:53:52Z
dc.date.available2019-09-17T15:53:52Z
dc.date.created2019-05
dc.date.issued2019-05-10
dc.date.submittedMay 2019
dc.date.updated2019-09-17T15:53:52Z
dc.description.abstractNitrogen-substituted alkynes are a unique class of compounds that have found general use in organic synthesis. The catalytic synthesis of N-substituted alkynes offers a rapid and step-efficient approach for accessing this structural motif. To better understand the synthesis and reactivity profile of N-alkynyl pyrroles, a study of the Cu-catalyzed coupling of pyrroles with 1-bromoalkynes was conducted and the scope uncovered. Subsequently, N-alkynyl pyrroles were applied to the synthesis of pyrrole[2,1-c]oxazin-1-ones and the formal total synthesis of the natural product peramine. Additionally, an N-alkynyl pyrrole was applied toward the synthesis of the pyrrole spiroketal alkaloid shensongine A. The α-alkylation of ketones is an indispensible C-C bond forming process to organic chemists. This process generally involves the formation of an enolate and subsequent alkylation with an electrophile. While very efficient, this series of steps generates a significant amount of waste that is often not on the radar of the typical chemist. Recent work has begun to address this issue resulting in several new “green” α-alkylation procedures. In an effort to better understand the potential application of a C-H activation procedure towards the “green” alkylation of ketones a study of the C-H activation and subsequent alkylation and alkenylation of cyclic 1,2-diketones was conducted.
dc.description.departmentChemistry
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/2152/75872
dc.identifier.urihttp://dx.doi.org/10.26153/tsw/2974
dc.language.isoen
dc.subjectN-alkynyl pyrrole
dc.subjectCopper
dc.subjectRhodium
dc.titleN-alkynylations of substituted pyrroles with 1-bromo-1-alkynes and C-alkylations and C-alkenylations of cyclic 1,2-diketones
dc.typeThesis
dc.type.materialtext
thesis.degree.departmentChemistry
thesis.degree.disciplineChemistry
thesis.degree.grantorThe University of Texas at Austin
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy
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