Electrochemical reductive cross-coupling of acyl chlorides and sulfinic acids towards the synthesis of thioesters

Abstract

The construction of C–S bonds is an important process in synthetic, medicinal and materials chemistry. Thiols are usually employed as the starting materials to provide the S source. However, their unpleasant smell and toxicity drive us to look for alternatives. In this context, we used an electrochemical reduction method to obtain thiyl radicals from sulfinic acids. In a simple undivided cell, various acyl chlorides and sulfinic acids were compatible, generating 40 examples of the desired thioesters in up to 95% yields. Preliminary mechanism studies suggested that the formation of thiyl radical species from sulfinic acid proceeded via multiple steps of a single electron transfer process.