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March 27, 2026The Journal of Organic Chemistry2 citations

N -(Difluoromethylthio)saccharin: Design, Synthesis, and Applications in Electrophilic Difluoromethylthiolation of Alkynes for the Construction of 4-Difluoromethylthiolated Isoxazoles

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WFWeijun FuMZMei ZhuYTYunfei Tian

Key Points

  • This research aims to develop an efficient reagent for the synthesis of 4-difluoromethylthiolated isoxazoles through electrophilic difluoromethylthiolation.
  • Synthesis of N-(difluoromethylthio)saccharin from BnSCF2H and silver salt of saccharin.
  • Application of the reagent for oxidifluoromethylthiolation of alkynes.
  • Evaluation of the reaction under mild conditions with a wide range of substrates.
  • The protocol successfully produces 4-difluoromethylthiolated isoxazoles with good compatibility for various functional groups.
  • Mechanistic studies show the reaction proceeds via an electrophilic pathway.
  • The method is applicable to late-stage modifications of natural products and pharmaceuticals.

Abstract

A novel and highly electrophilic difluoromethylthiolating reagent, N-(difluoromethylthio)saccharin, which is easily synthesized from BnSCF2H and the silver salt of saccharin, was developed. With this reagent, we disclose a practical and straightforward approach to access 4-difluoromethylthiolated isoxazoles via direct oxidifluoromethylthiolation of alkynes under mild reaction conditions. This protocol exhibits a broad substrate scope and good functional group compatibility and can be applied to late-stage difluoromethylthiolation of alkynes derived from natural products and pharmaceuticals. Mechanistic studies revealed that the reaction occurred via an electrophilic reaction pathway.

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Cite This Study

Fu et al. (2026) studied this question.

synapsesocial.com/papers/69c61f2515a0a509bde17c4bhttps://doi.org/10.1021/acs.joc.6c00028
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