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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Photoinduced Azidosulfonylative Cyclization of 1,6-Dienes with Sulfonyl Azides
Noriaki Shimamoto1, Norihito Arichi1, Shinsuke Inuki1
1Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
None:
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.
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