The electrochemically selective C3-thiolation of quinolines

Abstract

An electrochemical method has been developed to achieve the C3-thiolation of quinoline compounds. Achievements of this new strategy included maximum atom economy, direct conversion, and the use of simple and readily available starting materials. Various aryl/alkyl/heteroaryl thiols and even diselenides were found to be amenable to this transformation within the conditions of an undivided cell, providing the C–S-bond-containing products in up to 84% yield. BF₃·OEt₂ played an apparently irreplaceable role as an additive. Cyclic voltammetry and mechanistic studies indicated that the intermediate from the cathodic reduction of quinolines may have been intercepted by thiols and disulfides.