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

Green Chemistry Pub Date: 2022-09-05 DOI: 10.1039/D2GC02424A

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.

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