Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride
Timothy Noël achieved the electrochemical oxidative coupling of thiols and potassium fluoride to form sulfonyl fluoride.
Sulfonyl fluorides are emerging as important reagents in chemical biology, owing to their capacity to undergo ‘click’-type reactions – i.e. Sulfur(VI) Fluoride Exchange (SuFEx) – with nucleophilic functions of biopolymers, such as peptides and proteins, in water or aqueous media. The group of Dr. Timothy Noël at the Eindhoven University of Technology (The Netherlands) was carrying out investigations towards the development of an electrochemical synthesis of sulfonamides and found that, using an electrolyte with BF4 counterion, traces of the sulfonyl fluoride product were observed in the GC-MS. This observation gave them the confidence that by tweaking the sulfonamide reaction conditions, they probably could steer product formation selectively to sulfonyl fluoride.