Chemoselective Silylzincation of Functionalized Terminal Alkynes Using Dianion-Type Zincate (SiBNOL-Zn-ate):  Regiocontrolled Synthesis of Vinylsilanes

Abstract

A regio- and chemoselective silylzincation reaction of various functionalized alkynes was developed using a newly designed dianion-type zincate. Silylzincation of terminal alkynes, followed by electrophilic trapping, proved to be a powerful tool for the one-pot, regiocontrolled generation of trisubstituted functionalized alkenes. The functionalized vinylzincate intermediate also undergoes copper- and palladium-catalyzed C-C bond-forming reactions in high yields and with high regio- and chemoselectivities.