title: From ketones to esters by a Cu-catalyzed highly selective C(CO)-C(alkyl) bond cleavage: aerobic oxidation and oxygenation with air.
abstract: 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. (18)O labeling experiments reveal that oxygenation occurs during this transformation. Preliminary mechanism studies indicate that two novel pathways are mainly involved in this process.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road 38, Beijing 100191, China.
authors.forename: Xiaoqiang
authors.initials: X
authors.lastname: Huang
authors.forename: Xinyao
authors.initials: X
authors.lastname: Li
authors.forename: Miancheng
authors.initials: M
authors.lastname: Zou
authors.forename: Song
authors.initials: S
authors.lastname: Song
authors.forename: Conghui
authors.initials: C
authors.lastname: Tang
authors.forename: Yizhi
authors.initials: Y
authors.lastname: Yuan
authors.forename: Ning
authors.initials: N
authors.lastname: Jiao
mesh_terms: D000388:Air; D002384:Catalysis; D004952:Esters; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D013379:Substrate Specificity
chemical_list: D004952:Esters; D007659:Ketones; D010100:Oxygen