Electrooxidative trifunctionalization of alkenes with N-chlorosuccinimide and ArSSAr/ArSH to α,β-dichloride arylsulfoxides

Abstract

An unprecedented electrochemical oxidative trifunctionalization of olefins with diaryl disulfides/aryl thiols and N-chlorosuccinimide in an aqueous system is developed. Two C–Cl bonds, one C–S bond, and one SO bond are produced simultaneously in one step from simple and commercially available starting materials with clean energy. This tandem methodology features as mild reaction conditions, transition metal and additional oxidant free, broad substrate scope, good functional group compatibility, and gram scale preparation.

Keywords

• Electrooxidation
• Alkenes functionalization
• Vicinal dichlorination
• Sulfoxidation
• Tandem reaction