Photosensitized 1,n-Fluorosulfonamidylimination of Alkenes to Access Amino-Aliphatic Sulfamoyl Fluorides Using Bifunctional Fluorosulfonamoyl Reagents.

This study reports a novel class of bench-stable, oxime ester-derived bifunctional fluorosulfamoyl reagents for photosensitized 1,n-fluorosulfonamidylimination of alkenes. Upon visible-light irradiation, these reagents undergo energy-transfer-mediated homolysis, simultaneously generating a transient fluorosulfonamide radical and a persistent iminyl radical. This dual-radical system enables efficient 1,2- and 1,4-fluorosulfonamidylimination of alkenes, thereby providing direct access to valuable amino-aliphatic sulfamoyl fluorides under mild conditions. The utility of this method is demonstrated by the late-stage modification of bioactive molecules and further diversification of products via SuFEx click chemistry and selective deprotection.