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Sulfonyl fluoride synthesis through electrochemical oxidative coupling of thiols and potassium fluoride

  • Gabriele Laudadio
  • , Aloisio de Andrade Bartolomeu
  • , Luuk Verwijlen
  • , Yiran Cao
  • , Kleber de Oliveira
  • , Timothy Noël (Corresponding author)

    Research output: Contribution to journal › Article › Academic › peer-review

    331 Downloads (Pure)

    Abstract

    Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.

    Original languageEnglish
    Pages (from-to)11832-11836
    Number of pages5
    JournalJournal of the American Chemical Society
    Volume141
    Issue number30
    DOIs
    Publication statusPublished - 13 Jul 2019

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