Synthesis of multi-substituted vinylsilanes via copper(i)-catalyzed hydrosilylation reactions of allenes and propiolate derivatives with silylboronates?

Chemical Communications Pub Date: 2014-05-15 DOI: 10.1039/C4CC01722F

Abstract

An efficient and general copper(I)-catalyzed method for the synthesis of multi-substituted vinylsilanes is reported. Multi-substituted allenes with electron-withdrawing groups and propiolate derivatives reacted well with (dimethylphenylsilyl)boronic acid pinacol ester to afford silyl-substituted butenoate derivatives and β-silyl-substituted acrylate derivatives, respectively. The corresponding products could be obtained in moderate to high yields and with good to excellent stereoselectivities.

Graphical abstract: Synthesis of multi-substituted vinylsilanes via copper(i)-catalyzed hydrosilylation reactions of allenes and propiolate derivatives with silylboronates
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