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March 21, 2026Organic Letters0 citations

SmI 2 /Sm-Mediated Desulfurative Fluoroarylation of Thioamides with Polyfluoroarenes via C═S/C─H Bond Cleavage

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YLYongqi LiangZQZhiming QiaoYGYu Gao

Key Points

  • The aim is to explore a new method for the desulfurative fluoroarylation of thioamides using samarium diiodide.
  • Utilized samarium diiodide to mediate reactions under ligand-free and base-free conditions.
  • Examined the reaction with various polyfluoroarenes and thioamides.
  • Assessed functional group tolerance and substrate scope.
  • Successfully demonstrated bond cleavage of C═S and C─H during fluoroarylation.
  • Produced C-C bonds while retaining the integrity of some C-H bonds.
  • Achieved excellent chemoselectivity, especially with tetrafluorinated aromatic hydrocarbons.

Abstract

A robust samarium diiodide/samarium-mediated desulfurative fluoroarylation of thioamides with polyfluoroarenes via C═S/C─H bond cleavage is reported. This method represents the first example of desulfurative fluoroarylation of thioamides induced by samarium diiodide/samarium. The reaction occurs under ligand-free and base-free conditions, and experimental results demonstrated that this method exhibits excellent functional group tolerance and a broad substrate scope. Particularly in the reaction with tetrafluorinated aromatic hydrocarbons, one C-H bond undergoes cleavage and reacts with the thioamide to form a C-C bond, while the other C-H bond remains intact, demonstrating the reaction system's excellent chemoselectivity.

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Cite This Study

Liang et al. (2026) studied this question.

synapsesocial.com/papers/69be38596e48c4981c678b4dhttps://doi.org/10.1021/acs.orglett.6c00581
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