Catalyst-free electrosynthesis of benzothiophenes from 2-alkenylaryl disulfides

Abstract

The synthesis of benzothiophenes through electrosynthesis under oxidant- and metal-free conditions has been discovered. Electrolysis of symmetrical 2-alkenylaryl disulfides using an undivided cell leads to the formation of the corresponding benzothiophenes in good to moderate yields with good functional group tolerance. The usefulness of this methodology was further investigated with a scale-up experiment, which delivered a similar result to that of the small scale reaction. Several mechanistic investigations including DFT calculations were carried out to elucidate the reaction mechanism.