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February 5, 2026Organic Letters0 citations

Organophotoredox-Catalyzed Alkylation of Vinylsulfur Pentafluoride: Expanding Access to SF 5 -Containing Aliphatic Molecules

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LVLaurianne VerretPPPascal PaquinMRMartin Le Roy

Key Points

  • To develop a method for synthesizing aliphatic SF5 compounds using an organophotoredox strategy.
  • Utilized a metal-free organophotoredox approach
  • Conducted alkylation of vinylsulfur pentafluoride
  • Prepared starting material from SF5-triflate precursor
  • Implemented mild reaction conditions
  • Assessed reaction under continuous-flow processing
  • Achieved diverse SF5-substituted alkanes
  • Produced compounds in moderate to good yields
  • Demonstrated tolerance to a broad range of functional groups

Abstract

The pentafluorosulfanyl (SF5) group is a valuable fluorinated motif, but aliphatic SF5 synthesis remains challenging. We report a metal-free organophotoredox strategy to access aliphatic SF5 compounds via alkylation of vinylsulfur pentafluoride, prepared from an SF5-triflate precursor. This operationally simple transformation proceeds under mild conditions, tolerates a broad range of functional groups, and affords diverse SF5-substituted alkanes in moderate to good yields. The reaction is amenable to continuous-flow processing.

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Cite This Study

Verret et al. (2026) studied this question.

synapsesocial.com/papers/698433a5f1d9ada3c1fb0ff0https://doi.org/10.1021/acs.orglett.6c00153
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Also Consider

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

  1. 1Silyl Chloroalkenyl and Alkynyl Sulfur Pentafluorides as versatile reagents to access novel fundamental SF5 building blocks2025
  2. 2Photoredox Catalytic Hydropentafluorosulfanylation of Alkynes by Sulfur Hexafluoride2025
  3. 3Photocatalytic Diverse Synthesis of Transformable SF5-Scaffolds Utilizing SF62025
  4. 4Photoredox Catalytic Hydropentafluorosulfanylation of Alkynes by Sulfur Hexafluoride2026
  5. 5Single‐Step Photoinduced Radical Pentafluorosulfanylation and Cyclization of Alkenes for the Synthesis of <scp> SF <sub>5</sub> </scp> ‐Containing Cyclic Sulfinamides <sup>†</sup>2026