Metal-free TEMPO-promoted C(sp³)-H amination to afford multisubstituted benzimidazoles

J Org Chem. 2014 May 16;79(10):4727-34. doi: 10.1021/jo5005179. Epub 2014 May 1.

Abstract

An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp(3) C-H and free N-H of readily available N(1)-benzyl/alkyl-1,2-phenylenediamines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Catalysis
  • Cyclic N-Oxides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Metals / chemistry*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Benzimidazoles
  • Cyclic N-Oxides
  • Metals
  • TEMPO