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March 19, 2026Organic Letters4 citations

Visible-Light-Driven ( E )-β-Trifluoromethylation of Enamides via In Situ Generated Sulfur(VI) Photosensitizers

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CWCaiwen WanCSChangtong ShaoRLRuolan Leng

Key Points

  • The aim is to achieve (E)-β-trifluoromethylation of enamides under visible light using in situ generated sulfur(VI) photosensitizers.
  • Utilized sodium trifluoromethanesulfinate for trifluoromethylation
  • Conducted reactions under visible light
  • Developed a continuous-flow synthesis process
  • Eliminated the need for external oxidants and catalysts
  • Assessed broad substrate compatibility
  • Achieved successful trifluoromethylation of enamides
  • Demonstrated scalability with gram-scale synthesis
  • Showed mild reaction conditions
  • Enabled a robust and catalyst-free paradigm for synthesis

Abstract

We report an autoinductive, visible-light-mediated (E)-β-trifluoromethylation of enamides using sodium trifluoromethanesulfinate. This protocol eliminates exogenous catalysts by leveraging an in situ generated pentacoordinate sulfur(VI) species as the photosensitizer. Characterized by mild conditions and broad substrate compatibility, the method exhibits promising scalability, as evidenced by a gram-scale continuous-flow synthesis. This oxidant- and catalyst-free strategy provides a robust, scalable paradigm for accessing valuable trifluoromethylated building blocks.

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Cite This Study

Wan et al. (2026) studied this question.

synapsesocial.com/papers/69bb9345496e729e629814fdhttps://doi.org/10.1021/acs.orglett.6c00782
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Also Consider

Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

  1. 1General Method for Selective C(sp2)–H Trifluoromethylation of Enamides via Visible Light Dual Photoredox/Nickel Catalysis2026
  2. 2Direct Photocatalytic Trifluoromethyl-Carboxylation of Enamides: A Gateway to alpha-Trifluoroethyl Phenylglycines2025
  3. 3Direct Photocatalytic Trifluoromethyl-Carboxylation of Enamides: A Gateway to α-Trifluoroethyl Phenylglycines2026
  4. 4Visible-Light-Induced Trifluoromethyloximation of Alkenes with Sodium Nitrite as Oxime Source2025
  5. 5Photosensitized 1,n-Fluorosulfonamidylimination of Alkenes to Access Amino-Aliphatic Sulfamoyl Fluorides Using Bifunctional Fluorosulfonamoyl Reagents2026