Stereoselective Synthesis of (Z)-1-Alkylseleno-1-alkenes by Ni-Catalyzed Coupling Reaction of (Z)-Dialkylselenoethenes with Organozinc Halides

Abstract

(Z)-Dialkylselenoethenes 2, prepared conveniently from the hydrozirconation of dialkylselenoacetylenes 1 with Cp₂Zr (H) Cl in THF followed by protonolysis, react readily at − 10°C in THF with organozinc halides in the presence of a catalytic amount of NiCl₂ (dppe) to give (Z)-1-alkylseleno-1-alkenes 3 with retention of the configuration.