TY - JOUR
T1 - Sulfonyl fluoride synthesis through electrochemical oxidative coupling of thiols and potassium fluoride
AU - Laudadio, Gabriele
AU - de Andrade Bartolomeu, Aloisio
AU - Verwijlen, Luuk
AU - Cao, Yiran
AU - de Oliveira, Kleber
AU - Noël, Timothy
PY - 2019/7/13
Y1 - 2019/7/13
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85070789341&partnerID=8YFLogxK
U2 - 10.1021/jacs.9b06126
DO - 10.1021/jacs.9b06126
M3 - Article
C2 - 31303004
SN - 0002-7863
VL - 141
SP - 11832
EP - 11836
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 30
ER -