Direct Synthesis of Monofluoromethylthioesters from Acyl Chlorides with Elemental Sulfur and Fluoroiodomethane

We report an unprecedented Ni‐catalyzed direct monofluoromethylthiolation of acyl chlorides, in situ generated from carboxylic acids, with elemental sulfur (S8) as the S source and fluoroiodomethane (ICH2F) as the CH2F radical source to produce a series of monofluoromethylthioesters in moderate to g...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-06, Vol.27 (24), p.n/a
Main Authors: Hu, Chen‐Chen, Zhang, Yu‐Yang, Fang, Zeguo, Qing, Feng‐Ling
Format: Article
Language:English
Subjects:
acyl chlorides
Carboxylic acids
Chlorides
cross-coupling
Functional groups
monofluoromethylthiolation
nickel catalysis
Substrates
Sulfur
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Summary:We report an unprecedented Ni‐catalyzed direct monofluoromethylthiolation of acyl chlorides, in situ generated from carboxylic acids, with elemental sulfur (S8) as the S source and fluoroiodomethane (ICH2F) as the CH2F radical source to produce a series of monofluoromethylthioesters in moderate to good yields. This approach features excellent functional group tolerance and broad substrate scope. Additionally, the late‐stage monofluoromethylthiolation of complex bioactive molecules can also be accomplished using this method. A practical nickel‐catalyzed synthesis of monofluoromethylthioesters from acyl chlorides has been developed. In this protocol, acyl chloride intermediates were initially formed and then subjected to the nickel‐catalyzed cross‐coupling reaction with S8 and ICH2F, delivering the corresponding products in moderate to high yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400296