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Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides
Song, Guoyong1; Chen, Dan1; Pan, Cheng-Ling1; Crabtree, Robert H.3; Li, Xingwei1,2
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
2010-11-05
DOI10.1021/jo101596d
Volume75Issue:21Pages:7487-7490
Indexed BySCI ; IC ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordH BOND-CLEAVAGE ; C-H ; INTERNAL ALKYNES ; BENZOIC-ACIDS ; ACTIVATION ; COUPLING/CYCLIZATION ; ARYLATION ; CYCLOADDITION ; TEMPERATURE ; DERIVATIVES
AbstractA 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.
Language英语
WOS IDWOS:000283531100064
Citation statistics
Cited Times:196[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/141727
Collection中国科学院大连化学物理研究所
Affiliation1.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
GB/T 7714
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.
APA Song, Guoyong,Chen, Dan,Pan, Cheng-Ling,Crabtree, Robert H.,&Li, Xingwei.(2010).Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides.JOURNAL OF ORGANIC CHEMISTRY,75(21),7487-7490.
MLA Song, Guoyong,et al."Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides".JOURNAL OF ORGANIC CHEMISTRY 75.21(2010):7487-7490.
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