Efficient Ruthenium-Catalyzed Aerobic Oxidation of Alcohols Using a Biomimetic Coupled Catalytic System
- 5 February 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (5), 1657-1662
- https://doi.org/10.1021/jo0163750
Abstract
Efficient aerobic oxidation of alcohols was developed via a biomimetic catalytic system. The principle for this aerobic oxidation is reminiscent of biological oxidation of alcohols via the respiratory chain and involves selective electron/proton transfer. A substrate-selective catalyst (ruthenium complex 1) dehydrogenates the alcohol, and the hydrogens abstracted are transferred to an electron-rich quinone (4b). The hydroquinone thus formed is continuously reoxidized by air with the aid of an oxygen-activating Co−salen type complex (6). Most alcohols are oxidized to ketones in high yield and selectivity within 1−2 h, and the catalytic system tolerates a wide range of O2 concentrations without being deactivated. Compared to other ruthenium-catalyzed aerobic oxidations this new catalytic system has high turnover frequency (TOF).This publication has 38 references indexed in Scilit:
- X-ray Structure and Reactivity of (η4-tetraphenylcyclopentadienone)(CO)2Ru(HOCHMe2): Unexpected Stability of the Neutral 2-Propanol−Ruthenium(0) Complex with Respect to β-Hydride EliminationOrganometallics, 2001
- Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins by H2O2 Using a Biomimetic Flavin-Based Coupled Catalytic SystemJournal of the American Chemical Society, 2001
- A New Coupled Catalytic System for Dihydroxylation of Olefins by H2O2Journal of the American Chemical Society, 1999
- Ruthenium-Catalyzed Oxidation of Nonactivated Alcohols by MnO2The Journal of Organic Chemistry, 1994
- Palladium-catalyzed allylic oxidation of cyclohexenes using molecular oxygen as oxidantThe Journal of Organic Chemistry, 1990
- Multistep electron transfer in palladium-catalyzed aerobic oxidations via a metal macrocycle quinone systemJournal of the American Chemical Society, 1990
- X-ray crystal structure determination of (Ph4C4CO)Ru(CO)2(NHEt2). A reactive catalytic intermediate in transalkylation of aminesOrganometallics, 1988
- The selective oxidation of primary alcohols to aldehydes by oxygen employing a trinuclear ruthenium carboxylate catalystJournal of the American Chemical Society, 1987
- (Cyclopentadienone)ruthenium carbonyl complexes - a new class of homogeneous hydrogenation catalystsOrganometallics, 1985
- Homogeneous catalytic oxidation of amines and secondary alcohols by molecular oxygenJournal of the Chemical Society, Chemical Communications, 1978