Alkynylsilanes as Convenient Precursors for the Stereoselective Synthesis of (E)-Disubstituted Alkenes

Abstract

Hydromagnesiation of alkynylsilanes 1 gives (Z)-α-silylvinyl Grignard reagents 2, which are reacted with alkyl iodides or aryl iodides in the presence of CuI or Pd(PPh3)4 catalysts to afford (Z)-1,2-disubstituted vinylsilanes 3 in good yields. Intermediates 3 can undergo a desilylation reaction to give (E)-disubstituted alkenes 4 in high yields.