Metal-free oxygenation of cyclohexane with oxygen catalyzed by 9-mesityl-10-methylacridinium and hydrogen chloride under visible light irradiation

Chem Commun (Camb). 2011 Aug 14;47(30):8515-7. doi: 10.1039/c1cc12534f. Epub 2011 Jul 1.

Abstract

Photooxygenation of cyclohexane by O(2) occurs efficiently under visible-light irradiation of an O(2)-saturated acetonitrile solution containing 9-mesityl-10-methylacridinium ions (Acr(+)-Mes) and HCl to yield cyclohexanone, cyclohexanol and hydrogen peroxide. The photocatalytic reaction is initiated by electron transfer from Cl(-) to the mesitylene radical cation moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry
  • Acridines / chemistry*
  • Catalysis
  • Cyclohexanes / chemistry*
  • Cyclohexanols / chemistry
  • Cyclohexanones / chemistry
  • Electron Transport
  • Hydrochloric Acid / chemistry*
  • Hydrogen Peroxide / chemistry
  • Light*
  • Oxygen / chemistry*

Substances

  • 9-mesityl-10-methylacridinium
  • Acetonitriles
  • Acridines
  • Cyclohexanes
  • Cyclohexanols
  • Cyclohexanones
  • Cyclohexane
  • cyclohexanone
  • Hydrogen Peroxide
  • Hydrochloric Acid
  • Oxygen
  • acetonitrile