Electrochemical Conversions of Sulfinamidines into Sulfonimidoyl Fluorides

Sulfonimidoyl fluorides, the chiral aza-isosteres of sulfonyl fluorides, have gained increasing attention as a powerful linkage agent in the sulfur(VI)-fluoride exchange reaction (SuFEx). The hexavalent sulfonimidoyl fluorides are typically prepared from organosulfur in high oxidation states. We report herein an electrochemical approach using the readily available, bench-stable, yet underexplored tetravalent sulfinamidines without external chemical oxidants. The usefulness of the obtained sulfonimidoyl fluorides is demonstrated by their versatile SuFEx reactivity.