Proton addition to silylstyrenes: Overcoming the predilection for protiodesilylation

Normally, organosilyl nucleophiles such as vinylsilanes and allylsilanes undergo protiodesilylation reactions with protons. To favour addition reactions under these conditions, the ligands on silicon have been modified such that the leaving group ability and, simultaneously, the β-effect of the silyl group is reduced. In the case of allylsilanes, the use of dichlorosilyl groups does not significantly favour addition over substitution processes …