Efficient Ruthenium-Catalyzed Aerobic Oxidation of Alcohols Using a Biomimetic Coupled Catalytic System

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 co...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-03, Vol.67 (5), p.1657-1662
Main Authors: Csjernyik, Gábor, Éll, Alida H, Fadini, Luca, Pugin, Benoit, Bäckvall, Jan-E
Format: Article
Language:English
Subjects:
Aerobiosis
Alcohols - chemical synthesis
Alcohols - chemistry
Catalysis
Chemical reactivity
Chemistry
Exact sciences and technology
Hydroquinones - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Organic chemistry
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Oxidation-Reduction
Reactivity and mechanisms
Ruthenium - chemistry
Spin Labels
Substrate Specificity
Time Factors
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Summary: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).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0163750