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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
Huang, Xiaoqiang1; Li, Xinyao1; Zou, Miancheng1; Song, Song1; Tang, Conghui1; Yuan, Yizhi1; Jiao, Ning1,2
刊名JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
2014-10-22
DOI10.1021/ja50730041
136期:42页:14858-14865
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Multidisciplinary
资助者National Natural Science Foundation of China ; National Young Top-notch Talent Support Program ; Ph.D. Programs Foundation of the Ministry of Education of China ; National Natural Science Foundation of China ; National Young Top-notch Talent Support Program ; Ph.D. Programs Foundation of the Ministry of Education of China
研究领域[WOS]Chemistry
关键词[WOS]CARBON-CARBON BOND ; MOLECULAR-OXYGEN ; TERMINAL ALKYNES ; DIOXYGEN ACTIVATION ; ORGANIC-CHEMICALS ; OXIDASE CATALYSIS ; ALPHA-KETOAMIDES ; METHYL KETONES ; ARYL BROMIDES ; HALLER-BAUER
英文摘要

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.

语种英语
所属项目编号21325206 ; 21172006 ; 20120001110013
资助者National Natural Science Foundation of China ; National Young Top-notch Talent Support Program ; Ph.D. Programs Foundation of the Ministry of Education of China ; National Natural Science Foundation of China ; National Young Top-notch Talent Support Program ; Ph.D. Programs Foundation of the Ministry of Education of China
WOS记录号WOS:000343686500041
引用统计
被引频次:85[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/66720
专题北京大学药学院
作者单位1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
推荐引用方式
GB/T 7714
Huang, Xiaoqiang,Li, Xinyao,Zou, Miancheng,et al. From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)-C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2014,136(42):14858-14865.
APA Huang, Xiaoqiang.,Li, Xinyao.,Zou, Miancheng.,Song, Song.,Tang, Conghui.,...&Jiao, Ning.(2014).From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)-C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,136(42),14858-14865.
MLA Huang, Xiaoqiang,et al."From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)-C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 136.42(2014):14858-14865.
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