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

Authors

Chae S. Yi, Marquette UniversityFollow
Ki Hyeok Kwon, Marquette UniversityFollow
Do W. Lee, Marquette UniversityFollow

Document Type

Article

Language

eng

Format of Original

3 p.

Publication Date

4-2-2009

Publisher

American Chemical Society

Source Publication

Organic Letters

Source ISSN

1523-7060

Original Item ID

DOI: 10.1021/ol900097y

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 (k_H/k_D = 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

Accepted version. Organic Letters, Vol. 11, No. 7 (April 2, 2009): 1567-1569. DOI. © 2009 American Chemical Society. Used with permission.

Recommended Citation

Yi, Chae S.; Kwon, Ki Hyeok; and Lee, Do W., "Aqueous Phase C-H Bond Oxidation Reaction of Arylalkanes Catalyzed by a Water-Soluble Cationic Ru(III) Complex [(pymox-Me₂)₂RuCl₂]⁺BF₄^-" (2009). Chemistry Faculty Research and Publications. 373.
https://epublications.marquette.edu/chem_fac/373