Photocatalytic hydro-fluorosulfonylation of alkenes with N-fluorosulfonyl aldimines

Abstract

With the rise of SuFEx click chemistry, the development of efficient methods for incorporating fluorosulfonyl motifs into molecules has become increasingly significant. Herein, we report a photocatalytic hydro-fluorosulfonylation of alkenes enabled by using N-fluorosulfonyl aldimines (NFSAs) as readily available fluorosulfonylation reagents. This method allows for the rapid formation of a diverse range of aliphatic sulfonyl fluorides from alkenes under mild photocatalytic conditions. The practicality of this approach is demonstrated through the late-stage hydro-fluorosulfonylation of complex molecules and the straightforward synthesis of PROTAC-like compounds via intermolecular SuFEx ligations. Green metrics calculations indicate that our method, which utilizes N-fluorosulfonyl aldimines as novel radical reagents, generates less waste and requires a smaller total mass of chemicals, thereby enhancing overall atom efficiency.