Journal
GREEN CHEMISTRY
Volume 24, Issue 19, Pages 7350-7354Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc02424a
Keywords
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Funding
- National Key R&D Program of China [2021YFA1500100]
- National Natural Science Foundation of China [22031008]
- Science Foundation of Wuhan [2020010601012192]
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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.
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.
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