A Free-Radical-Promoted Stereospecific Decarboxylative Silylation of α,β-Unsaturated Acids with Silanes

A stereospecific decarboxylative silylation of acrylic and propiolic acids with silanes was developed. This reaction represents the first example of decarboxylative C-Si bond formation and provides an efficient and convenient approach to various synthetically useful alkenyl and alkynyl organo-silicon compounds through the reaction of alpha,beta-unsaturated acids with silanes. Spin-trapping and EPR experiments support a radical addition/elimination process.