Effect of L-cysteine on the oxidation of cyclohexane catalyzed by manganeseporphyrin

Bioorg Med Chem Lett. 2015 Jun 1;25(11):2356-9. doi: 10.1016/j.bmcl.2015.04.020. Epub 2015 Apr 12.

Abstract

Effect of L-cysteine as the cocatalyst on the oxidation of cyclohexane by tert-butylhydroperoxide (TBHP) catalyzed by manganese tetraphenylporphyrin (MnTPP) has been investigated. The results showed that L-cysteine could moderately improve the catalytic activity of MnTPP and significantly increase the selectivity of cyclohexanol. Different from imidazole and pyridine, the L-cysteine may perform dual roles in the catalytic oxidation of cyclohexane. Besides as the axial ligand for MnTPP, the L-cysteine could also react with cyclohexyl peroxide formed as the intermediate to produce alcohol as the main product.

Keywords: Biomimetic catalysis; Cocatalyst; Manganese tetra-phenylporphyrin; Selective oxidation; l-Cysteine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclohexanes / chemistry*
  • Cysteine / chemistry*
  • Manganese / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Porphyrins / chemistry*

Substances

  • Cyclohexanes
  • Porphyrins
  • Manganese
  • Cyclohexane
  • Cysteine