Preparation and regioselective metalation of bis(trimethylsilyl)methyl-substituted aryl derivatives

Abstract

A range of bis(trimethylsilyl)methyl-substituted aryl derivatives was prepared by using a Kumada-Corriu cross-coupling reaction. The regioselective metalation of the resulting bis(trimethylsilyl)methyl-substituted aryl derivatives bearing this bulky silyl group allowed the generation of functionalized aromatics. A regioselective switch in the presence or in the absence of the bis(trimethylsilyl)methyl group has been demonstrated. Furthermore, this silyl group was converted into a formyl group or a styryl group, enhancing the scope of application of such bis(trimethylsilyl)methyl-substituted arenes.

Keywords: aromatics; lithiation; magnesium; metalation; silyl reagents.