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

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.