Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 42, Pages 14858-14865Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5073004
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Funding
- National Natural Science Foundation of China [21325206, 21172006]
- National Young Top-notch Talent Support Program
- Ph.D. Programs Foundation of the Ministry of Education of China [20120001110013]
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The Cu-catalyzed aerobic oxidative esterification of simple ketones via C-C bond cleavage has been developed. Varieties of 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, electron-deficient phenols, as well as various natural alcohols. The usage of inexpensive copper catalyst, broad substrate scope, and neutral and open air conditions make this protocol very practical. O-18 labeling experiments reveal that oxygenation occurs during this transformation. Preliminary mechanism studies indicate that two novel pathways are mainly involved in this process.
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