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C-SuFEx linkage of sulfonimidoyl fluorides and organotrifluoroborates

Author

Listed:
  • Suqin Zhao

    (East China Normal University)

  • Daming Zeng

    (East China Normal University)

  • Ming Wang

    (East China Normal University)

  • Xuefeng Jiang

    (East China Normal University
    China; East China Normal University
    Henan Normal University)

Abstract

Sulfur(VI) fluoride exchange, a new type of linkage reaction, has excellent potential for application in functional molecule linkage to prepare pharmaceuticals, biomolecules, and polymers. Herein, a C-SuFEx reaction is established to achieve fast (in minutes) linkage between sulfonimidoyl fluorides and aryl/alkyl organotrifluoroborates. Potassium organotrifluoroborates are instantaneously activated via a substoichiometric amount of trimethylsilyl triflate to afford organodifluoroboranes, releasing BF3 as an activating reagent in situ. This sulfur(VI) fluoride exchange technique is capable of forming S(VI)-C(alkyl), S(VI)-C(alkenyl) and S(VI)-C(aryl) bonds, demonstrating its broad scope. Natural products and pharmaceuticals with sensitive functional groups, such as valdecoxib, celecoxib and diacetonefructose, are compatible with this protocol, allowing the formation of diverse sulfoximines.

Suggested Citation

  • Suqin Zhao & Daming Zeng & Ming Wang & Xuefeng Jiang, 2024. "C-SuFEx linkage of sulfonimidoyl fluorides and organotrifluoroborates," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-44998-6
    DOI: 10.1038/s41467-024-44998-6
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