期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 10, 期 4, 页码 1004-1009出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201403245
关键词
alcohols; copper; homogeneous catalysis; oxidation; radicals
资金
- MEXT, Japan
- JSPS Asian Core Program on Cutting-Edge Organic Chemistry in Asia
- [24390001]
- [25860001]
- Grants-in-Aid for Scientific Research [14J06364, 25860001] Funding Source: KAKEN
The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2-azaadamantane N-oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper-catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom-rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.
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