Title

Aqueous Phase C-H Bond Oxidation Reaction of Arylalkanes Catalyzed by a Water-Soluble Cationic Ru(III) Complex [(pymox-Me2)2RuCl2]+BF4-

Document Type

Article

Publication Date

4-2-2009

Source Publication

Organic Letters

Source ISSN

1523-7060

Abstract

The cationic complex [(pymox-Me2)RuCl2]+BF4 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 PhCOCH3 at room temperature. Both a large kinetic isotope effect (kH/kD = 14) and a relatively large Hammett value (ρ = −1.1) suggest a solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo intermediate species.

Comments

Organic Letters, Vol. 11, No. 7 (April 2, 2009): 1567-1569. DOI.