Cobalt- and iron-catalyzed redox condensation of o-substituted nitrobenzenes with alkylamines: a step- and redox-economical synthesis of diazaheterocycles

Org Lett. 2013 Dec 20;15(24):6218-21. doi: 10.1021/ol403064z. Epub 2013 Nov 14.

Abstract

A wide variety of functionalized 2-aryl benzimidazoles can be prepared by a solvent-free cobalt- or iron-catalyzed redox condensation of 2-nitroanilines and benzylamines. The cascade including benzylamine oxidation, nitro reduction, condensation, and aromatization occurs without any added reducing or oxidizing agent. The method can be extended to other alkylamines as reducing components or 2-nitrobenzamides as oxidizing components when using an iron/sulfur catalyst to afford various diazaheterocycles.

MeSH terms

  • Amines / chemistry*
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Catalysis
  • Cobalt / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Iron / chemistry*
  • Molecular Structure
  • Nitrobenzenes / chemistry*
  • Oxidation-Reduction

Substances

  • Amines
  • Aza Compounds
  • Heterocyclic Compounds
  • Nitrobenzenes
  • Cobalt
  • Iron