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Updated: Aug 5, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Intermolecular Aza Paternò-Büchi Reaction of N‑(Fluorosulfonyl)imines and Triplet-State Aromatic Alkenes
Hiroto Kimura1,2, Yasuhiro Yamauchi1, Takuya Hashimoto1,2,3
1Molecular Synthesis and Function Laboratory, RIKEN Pioneering Research Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Abstract:
Intermolecular aza Paternò-Büchi reaction between N-(fluorosulfonyl)-imines and aromatic alkenes has been developed through the photoinduced generation of a triplet state of the aromatic alkene. The N-fluorosulfonyl group proved crucial in enabling this transformation to furnish azetidines, as no product formation was observed in the reaction using N-tosylimines. Theoretical studies revealed that the highly electrophilic fluorosulfonyl-substituted nitrogen facilitates efficient nitrogen-carbon bond formation with triplet-state styrenes. Furthermore, by taking advantage of facile derivatization of the fluorosulfonyl group, we demonstrated its reductive deprotection to generate unprotected azetidines.
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