Aqueous phase C-H bond oxidation reaction of arylalkanes catalyzed by a water-soluble cationic Ru(III) complex [(pymox-Me2)2RuCl2]+BF4-

Org Lett. 2009 Apr 2;11(7):1567-9. doi: 10.1021/ol900097y.

Abstract

The cationic complex [(pymox-Me(2))RuCl(2)](+)BF(4)(-) was found to be a highly effective catalyst for the C-H bond oxidation reaction of arylalkanes in water. For example, the treatment of ethylbenzene (1.0 mmol) with t-BuOOH (3.0 mmol) and 1.0 mol % of the Ru catalyst in water (3 mL) cleanly produced PhCOCH(3) at room temperature. Both a large kinetic isotope effect (k(H)/k(D) = 14) and a relatively large Hammett value (rho = -1.1) suggest a solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo intermediate species.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkanes / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Kinetics
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Ruthenium / chemistry*
  • Water / chemistry

Substances

  • Alkanes
  • Organometallic Compounds
  • Water
  • Ruthenium