LiClO 4 · 3H 2O promoted highly regioselective ring-opening of epoxides with thiols under neutral conditions

Abstract

A simple, rapid, atom economy and highly efficient procedure has been developed for thiolysis of epoxides by aromatic and aliphatic thiols under solvent-free conditions. A high regioselectivity in favor of nucleophilic attack at the benzylic carbon atom of aromatic epoxides, such as styrene oxide, is observed. However, aliphatic unsymmetrical alkenyl oxides undergo selective nucleophilic attack at the sterically less hindered carbon atom. A variety of β-hydroxy sulfides were obtained in short reaction time and excellent yields with nearly complete regioselectivity.