A Mild Catalytic Oxidation System: FePcOTf/H2O2 Applied for Cyclohexene Dihydroxylation

Molecules. 2015 May 11;20(5):8429-39. doi: 10.3390/molecules20058429.

Abstract

Iron (III) phthalocyanine complexes were employed for the first time as a mild and efficient Lewis acid catalyst in the selective oxidation of cyclohexene to cyclohexane-1,2-diol. It was found that the catalyst FePcOTf shown excellent conversion and moderate selectivity relative to other iron (III) phthalocyanine complexes. The optimum conditions of the oxidation reaction catalyzed by FePcOTf/H2O2 have been researched in this paper. Iron (III) phthalocyanine triflate (1 mol %) as catalyst, hydrogen peroxide as oxidant, methanol as solvent, and a mole ratio of substrate and oxidant (H2O2) of 1:1 were used for achieving moderate yields of 1,2-diols under reflux conditions after eight hours.

Keywords: cyclohexane-1,2-diols; cyclohexene; iron (III) phthalocyanine; triflate.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Cyclohexanes / chemical synthesis
  • Cyclohexenes / chemistry*
  • Ferrous Compounds / chemistry*
  • Hydrogen Peroxide / chemistry
  • Hydroxylation / physiology*
  • Indoles / chemistry*
  • Lewis Acids / chemistry
  • Oxidation-Reduction

Substances

  • Cyclohexanes
  • Cyclohexenes
  • Ferrous Compounds
  • Indoles
  • Lewis Acids
  • iron phthalocyanine
  • cyclohexene
  • Cyclohexane
  • Hydrogen Peroxide