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 journalArticleAcademicpeer-review

25 Citations (Scopus)
31 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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