Cu-Catalyzed Regiodivergent and Stereoselective Silylation of 2,3-Disubstituted 1,3-Dienes

Abstract

Regiodivergent silylation of conjugated dienes represents an elegant and straight forward approach to access diverse organosilicon compounds. While the silylation of 1- or 2- substituted conjugated dienes has been well developed, the silylation of sterically more demanding 2,3-disubstituted dienes was unknown. Here, we disclosed a Cu-catalyzed regiodivergent protosilylation of 2,3-disubstituted dienes, delivering 2,1- and 4,1- protosilylation compounds regioselectively and stereoselectively. Moreover, 4,1-borosilylation with excellent regio- and stereoselectivity was also achieved by the absence of electrophile under similar conditions of 2,1-protosilylation. Our method would like to provide efficient approaches for the synthesis of structurally diverse organosilicon compounds, which would devote in fulfilling the map of conjugated dienes silylation.