Direct Transfer of the Sulfonylimino Group of Imino-λ³-Bromane to <i>N</i>-Heterocycles and Trialkylamines: Synthesis of <i>N</i>-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.