TY - JOUR
T1 - Highly efficient aerobic oxidation of alcohols by using less-hindered nitroxyl-radical/copper catalysis
T2 - Optimum catalyst combinations and their substrate scope
AU - Sasano, Yusuke
AU - Kogure, Naoki
AU - Nishiyama, Tomohiro
AU - Nagasawa, Shota
AU - Iwabuchi, Yoshiharu
N1 - Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/4
Y1 - 2015/4
N2 - 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.
AB - 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.
KW - alcohols
KW - copper
KW - homogeneous catalysis
KW - oxidation
KW - radicals
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U2 - 10.1002/asia.201403245
DO - 10.1002/asia.201403245
M3 - Article
C2 - 25620279
AN - SCOPUS:84925446260
VL - 10
SP - 1004
EP - 1009
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 4
ER -