Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 5, Pages 1657-1662Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0163750
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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 O-2 concentrations without being deactivated. Compared to other ruthenium-catalyzed aerobic oxidations this new catalytic system has high turnover frequency (TOF).
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