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

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.

Automated summary

The construction of C-S bonds plays a crucial role in synthetic, medicinal, and materials chemistry. In this study, we used an electrochemical reduction method to obtain thiyl radicals from sulfinic acids. This approach enabled the synthesis of a variety of desired thioesters in high yields. The preliminary mechanism studies revealed that the formation of thiyl radical species from sulfinic acid involved multiple steps of a single electron transfer process.