Borane-promoted C(sp3)−H hydride abstraction

Kustiana, Betty 2022. Borane-promoted C(sp3)−H hydride abstraction. PhD Thesis, Cardiff University. Item availability restricted.

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Abstract

This thesis describes the utility of tris(pentafluorophenyl)borane, B(C6F5)3, for the development of new catalytic methods of C(sp3 )−H activation via hydride abstraction for alkene isomerization. Chapter 1 introduces boranes and organoboranes applications in stoichiometric and catalytic transformations, including B(C6F5)3 utility in both stoichiometric and catalytic applications of C(sp3 )−H activation of cyclohexa-1,4-diene and /-amino scaffolds via hydride abstraction. Chapter 2 discusses (E)-selective isomerization of alkenes catalysed by B(C6F5)3. In total, more than 40 examples with various functional groups have been reported. This method provides a metal-free isomerization process of various synthetically useful compounds with the highly stereo-controlled process. The mechanistic study will also be discussed to propose the isomerization mechanism. Chapter 3 describes the exploration of B(C6F5)3 application for the catalytic (E)-selective isomerization of allyl heteroatom substrates consisting of allyl silanes and allyl germanes. The derivatizations of products to show their utility in the organic synthesis are also presented, including C-C (one-pot Isomerization/Hiyama cross-coupling) and C-O (epoxidation) bond formations. In addition, the investigation for isomerization of several allyl heteroatoms (O, S, N) and propargyl substrates will also be presented. Finally, chapter 4 describes the experimental and characterization data.

Item Type:	Thesis (PhD)
Date Type:	Completion
Status:	Unpublished
Schools:	Chemistry
Date of First Compliant Deposit:	22 August 2023
Last Modified:	22 Aug 2024 01:30
URI:	https://orca.cardiff.ac.uk/id/eprint/161976

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