Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

• Published in: Journal of the American Chemical Society Vol. 141; no. 30; pp. 11832 - 11836
• Main Authors: Laudadio, Gabriele, Bartolomeu, Aloisio de A, Verwijlen, Lucas M. H. M, Cao, Yiran, de Oliveira, Kleber T, Noël, Timothy
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 31.07.2019; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Communication; Physical Sciences; Science & Technology; CATALYSIS; FLUORINATION; THIOSULFONATES; SUFEX; DISULFIDES
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/jacs.9b06126

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.