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Direct Transfer of the Sulfonylimino Group of Imino-λ3-Bromane to N-Heterocycles and Trialkylamines: Synthesis of N-Iminoammonium Ylides under Metal-Free Conditions

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posted on 15.01.2009, 00:00 authored by Masahito Ochiai, Yufuko Kawano, Takao Kaneaki, Norihiro Tada, Kazunori Miyamoto
Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-λ3-bromane at room temperature results in direct transfer of the sulfonylimino group to the nitrogen atoms and affords a variety of iminoammonium ylides under transition-metal-free conditions. The imino-λ3-bromane probably serves as an active nitrenoid species without any activation and produces the ammonium ylides via a bimolecular nucleophilic substitution process.