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 organosilicon compounds through the reaction of α,β‐unsaturated acids with silanes. Spin‐trapping and EPR experiments support a radical addition/elimination process. A radical transformation: A stereospecific decarboxylative silylation of acrylic and propiolic acids with silanes was developed. This method provides an efficient and convenient approach to various synthetically useful alkenyl and alkynyl organosilicon compounds through the reaction of α,β‐unsaturated acids with silanes. Spin‐trapping and EPR experiments support a radical addition/elimination process.