Ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid

SI Murahashi; N Komiya; Y Oda; T Kuwabara; T Naota

doi:10.1021/jo001348f

Ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid

J Org Chem. 2000 Dec 29;65(26):9186-93. doi: 10.1021/jo001348f.

Authors

SI Murahashi¹, N Komiya, Y Oda, T Kuwabara, T Naota

Affiliation

¹ Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3, Machikaneyama, Toyonaka, Osaka 560-8531, Japan.

PMID: 11149868
DOI: 10.1021/jo001348f

Abstract

The ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid gives the corresponding ketones and alcohols highly efficiently at room temperature. The former catalytic system, RuCl(2)(PPh(3))(3)-t-BuOOH, is preferable to the oxidation of alkylated arenes to give aryl ketones. The latter system, Ru/C-CH(3)CO(3)H, is suitable especially for the synthesis of ketones and alcohols from alkanes. The ruthenium-catalyzed oxidation of cyclohexane with CH(3)CO(3)H in trifluoroacetic acid/CH(2)Cl(2) at room temperature gave cyclohexyl trifluoroacetate and cyclohexanone with 90% conversion and 90% selectivity (85:15). The mechanistic study indicates that these catalytic oxidations of hydrocarbons involve oxo-ruthenium species as key intermediates.