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学科主题: 药学
题名:
From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)-C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air
作者: Huang, Xiaoqiang1; Li, Xinyao1; Zou, Miancheng1; Song, Song1; Tang, Conghui1; Yuan, Yizhi1; Jiao, Ning1,2
刊名: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
发表日期: 2014-10-22
DOI: 10.1021/ja50730041
卷: 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
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
项目资助者: National Natural Science Foundation of China ; National Young Top-notch Talent Support Program ; Ph.D. Programs Foundation of the Ministry of Education of China
WOS记录号: WOS:000343686500041
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/66720
Appears in Collections:北京大学药学院_期刊论文

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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

Recommended Citation:
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.
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