Ruthenium-Catalyzed Oxidation of Alkanes with tert-Butyl Hydroperoxide and Peracetic Acid

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, RuCl2(PPh3)3-t-BuOOH, is preferable to the oxidation of alkylated arenes to give aryl ketone...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2000-12, Vol.65 (26), p.9186-9193
Main Authors: Murahashi, Shun-Ichi, Komiya, Naruyoshi, Oda, Yoshiaki, Kuwabara, Toshiyuki, Naota, Takeshi
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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, RuCl2(PPh3)3-t-BuOOH, is preferable to the oxidation of alkylated arenes to give aryl ketones. The latter system, Ru/C−CH3CO3H, is suitable especially for the synthesis of ketones and alcohols from alkanes. The ruthenium-catalyzed oxidation of cyclohexane with CH3CO3H in trifluoroacetic acid/CH2Cl2 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo001348f