A General Electrochemical Synthesis of Sulfonimidoyl Fluorides,Azides,and Acetates

Sulfonimidoyl fluorides,the aza-bioisostere of sulfonyl fluorides,are emerging as a promising linkage agent in the sulfur(VI)fluoride exchange reaction(SuFEx).However,conventional synthetic approaches typically require the use of either unstable sulfonimidoyl chlorides,toxic and corrosive sulfur fluorides,or expensive electrophilic fluorinating agents.Herein,we report an electrochemistry-enabled oxidative nucleophilic fluorination of readily available and bench-stable sulfinamides using a commercially available and easy-to-handle triethylamine trihydrofluoride.With other nucleophilic agents,this electrochemical approach also serves as a general approach to diverse sulfonimidoyl derivatives,including sulfonimidoyl azides and acetates.