Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Addition of Interelement Compounds Having B-Si, B-B, and Cl-S Bonds to Alkynes, and Subsequent Cross-Couplings

Abstract

Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts. The subsequent cross-coupling reactions of the boron-containing alkenes to install various aryl groups afforded the corresponding tri- and tetraarylated olefins. This account describes our research on the highly regio- and stereoselective synthesis of multifunctionalized olefins such as tetraarylethenes with four different aryl groups.

Keywords: alkynes; chlorothiolation; cross-coupling; diborylation; silaboration.