New approach to oximes through reduction of nitro compounds enabled by visible light photoredox catalysis

Org Lett. 2013 Jun 7;15(11):2660-3. doi: 10.1021/ol4009443. Epub 2013 May 24.

Abstract

A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)3Cl2 photocatalyst, Hünig's base, Mg(ClO4)2 activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry*
  • Light
  • Magnesium Compounds / chemistry
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Oxidation-Reduction
  • Oximes / chemical synthesis*
  • Oximes / chemistry
  • Perchlorates / chemistry
  • Photochemical Processes
  • Ruthenium / chemistry

Substances

  • Coordination Complexes
  • Magnesium Compounds
  • Nitro Compounds
  • Oximes
  • Perchlorates
  • magnesium perchlorate
  • Ruthenium