Zirconocene-Mediated Stereoselective Synthesis of Multisubstituted Vinylsilanes

Significance

Although di- or trisubstituted vinylsilanes have been employed for Hiyama coupling to access multisubstituted olefins, only few examples have been shown to synthesize stereodefined multisubstituted vinylsilanes. The authors developed a direct, regio- and stereoselective synthesis of tri- and tetrasubstituted vinylsilanes by a one-pot zirconocene-mediated carbometalation of alkynylsilanes and subsequent transformation with various electrophiles. They also demonstrate the utility of the vinylsilane product 2 by coupling it to iodobenzene to afford the disubstituted olefin 3 in excellent yield and stereoselec­tivity.