Electrochemically dehydrogenative C(sp2)–H/S–H cross-coupling: efficient synthesis of ortho-aminophenyl thioglycoside derivatives

Abstract

We have developed an electro-mediated method for synthesizing aryl thioglycosides through intermolecular anodic oxidative cross-dehydrogenative C(sp²)–S bond coupling reactions involving (un)protected 1-thiosugars and anilines. This protocol is sustainable without the use of external transition-metal catalysts or additional oxidants employed in previous methods. It demonstrates a broader substrate scope concerning both 1-thiosugars and anilines. Furthermore, the reaction is applicable to the late-stage functionalization of drugs. Mechanistic studies using cyclic voltammetry and control experiments reveal that a radical cross coupling process is implicated in this transformation.