Login / Signup

Iodine(III)-Catalyzed Oxidative Cyclization of Aryl Amines to Construct N -Alkylbenzimidazoles.

Carmen Margaret WhiteSherlyn CazaresEfren D Gonzalez-CortesTom G Driver
Published in: The Journal of organic chemistry (2024)
An I(III)-catalyzed oxidative cyclization reaction using selectfluor as the oxidant was developed that converts ortho -substituted anilines to benzimidazoles. The mild reaction requires as little as 0.5 mol % of iodobenzene, and its scope is broad: electron-withdrawing or electron-releasing groups on the aniline portion are tolerated, and cyclic or acyclic N -alkylamines are permitted as ortho -substituents. Preliminary mechanistic investigations suggest that benzimidazole formation occurs via cationic reactive intermediates, and an intramolecular kinetic isotope effect of 1.98 ± 0.05 was measured.
Keyphrases
  • electron transfer
  • molecular docking
  • room temperature
  • solar cells
  • electron microscopy
  • computed tomography
  • magnetic resonance imaging
  • dual energy
  • mass spectrometry
  • gas chromatography