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Cu(I)-NHC Catalysed Silylation of Allenes:A Novel Approach towards Vinylsilanes

Hu, Ya-Chu

[Thesis]. Manchester, UK: The University of Manchester; 2014.

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Abstract

This thesis describes the development of a novel Cu(I)-NHC catalysed silylation of allenes using a commercial available silylborane reagent and the synthesis of a range of vinylsilanes. During the development of the approach, a series of NHC ligands were synthesised and applied in reactions for optimizing the regioselectivity. Excellent regiocontrol was achieved with the use of a 7-membered cyclic NHC ligand. Moreover, a library of aryl allene derivatives synthesised in this work could be used in the Cu(I)-NHC catalysed silylation of allenes to afford a variety of vinylsilanes with high efficiency. Allylcoppper intermediates generated catalytically can be trapped by aldehydes to furnish homoallylic alcohols with high diastereoselectivity in a three-component coupling reaction. A range of vinylsilanes having significant potential in Hiyama cross-coupling and Fleming-Tamao oxidation reactions were successfully synthesised by the protocol of Cu(I)-NHC catalysed silylation of allenes and extension to the three-component coupling.