Preparation and Regioselective Metalation of Bis(trimethylsilyl)methyl-Substituted Aryl Derivatives

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