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From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)-C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air

Xiaoqiang Huang, Xinyao Li, Miancheng Zou, Song Song, Conghui Tang, Yizhi Yuan and Ning Jiao*

*State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China, Email: jiaoningbjmu.edu.cn

X. Huang, X. Li, M. Zou, S. Song, C. Tang, Y. Yuan, N. Jiao, J. Am. Chem. Soc., 2014, 136, 14858-14865.

DOI: 10.1021/ja5073004 (free Supporting Information)



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Abstract

In a Cu-catalyzed aerobic oxidative esterification of simple ketones via C-C bond cleavage, various common ketones, even inactive aryl long-chain alkyl ketones, are selectively converted into esters. The reaction tolerates a wide range of alcohols, including primary and secondary alcohols, chiral alcohols with retention of the configuration and electron-deficient phenols.

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Key Words

esters, oxidative esterification, oxygen


ID: J48-Y2014