Electrochemical Conversions of Sulfenamides into Sulfonimidoyl- and Sulfondiimidoyl Fluorides

亚磺酰胺电化学转化为磺酰亚胺氟化物和磺二酰亚胺氟化物

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Abstract

The invention of versatile linkage agents provides the chemical basis for SuFEx chemistry. Sulfonimidoyl fluorides and sulfondiimidoyl fluorides are aza-isosteres of sulfonyl fluorides with diverse reactivity through the fine-tuning of N-substituents. However, limited synthetic approaches impede their wide applications in SuFEx chemistry. Herein, we develop a straightforward electrochemical strategy for sulfonimidoyl- and sulfondiimidoyl fluorides through sequential oxidations of the readily available sulfenamides via sulfinamide and iminosulfinamide intermediates, respectively. The previously rarely investigated (bis)-sulfondiimidoyl fluorides are now easily accessible and readily participate in SuFEx chemistry with diverse oxygen and nitrogen nucleophiles, macrocyclization, and polymerization.

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