Photoinduced Azidosulfonylative Cyclization of 1,6-Dienes with Sulfonyl Azides

Electrophilic azides serve as valuable reagents in visible-light-induced photocatalytic processes. While the reactivity of triplet nitrenes formed via energy transfer to electrophilic azides has been relatively well studied, the synthetic potential of nitrene radical anions generated through single electron transfer remains less explored. Herein, we report a photoinduced azidosulfonylative cyclization of 1,6-dienes with sulfonyl azides in the presence of 9,10-diphenylanthracene as a photoreductant, providing access to functionalized five-membered heterocycles. Mechanistic studies suggest that nitrene radical anions are responsible for the generation of sulfonyl radicals through hydrogen atom transfer from N,N-dimethylformamide (DMF) solvent.