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

  • 10.1021/ol802383f
  • Org. Lett.
  • p 2-8, 11 (2), Issue 2,
  • Letter
Exposure of N-heterocycles and aliphatic trialkylamines to trifluoromethanesulfonylimino-λ 3 -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-λ 3 -bromane probably serves as an active nitrenoid species without any activation and produces the ammonium ylides via a bimolecular nucleophilic substitution process.