Electrochemical C(sp3)–S bond cleavage of thioethers: an approach for simultaneous utilization of carbon- and sulfur-fragments†

Abstract

The cleavage and utilization of C–S bonds is a critical challenge in synthetic chemistry, traditionally requiring metal catalysis and disposing of sulfur fragments as wastes. Herein, we report an electrochemical method for the regioselective cleavage of C(sp³)–S bonds of alkyl aryl thioethers under mild conditions. This electro-oxidative approach generates the corresponding cationic species of both C- and S-fragments after the cleavage of the C–S bonds. Subsequently, these species are captured by O-nucleophiles and converted into aldehydes/ketones and sulfinates. The simultaneous utilization of both C- and S-fragments not only significantly enhances the atom economy but also offers a sustainable alternative to traditional C–S bond cleavage strategies.