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题名: Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides
作者: Song, Guoyong1;  Chen, Dan1;  Pan, Cheng-Ling1;  Crabtree, Robert H.3;  Li, Xingwei1, 2
刊名: JOURNAL OF ORGANIC CHEMISTRY
发表日期: 2010-11-05
DOI: 10.1021/jo101596d
卷: 75, 期:21, 页:7487-7490
收录类别: SCI ;  IC ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C-H activation of benzamides has been developed. Ag(2)CO(3) proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl(2)](2), was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C-H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles.
关键词[WOS]: H BOND-CLEAVAGE ;  C-H ;  INTERNAL ALKYNES ;  BENZOIC-ACIDS ;  ACTIVATION ;  COUPLING/CYCLIZATION ;  ARYLATION ;  CYCLOADDITION ;  TEMPERATURE ;  DERIVATIVES
语种: 英语
WOS记录号: WOS:000283531100064
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/141727
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
2.Scripps Res Inst, Jupiter, FL 33458 USA
3.Yale Univ, Dept Chem, New Haven, CT 06520 USA

Recommended Citation:
Song, Guoyong,Chen, Dan,Pan, Cheng-Ling,et al. Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides[J]. JOURNAL OF ORGANIC CHEMISTRY,2010,75(21):7487-7490.
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