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Palladium-Catalyzed Coupling Reaction of alpha-Diazocarbonyl Compounds with Aromatic Boronic Acids or Halides
Peng, Cheng; Yan, Guobin; Wang, Yan; Jiang, Yubo; Zhang, Yan; Wang, Jianbo
关键词Palladium Catalysis Cross-coupling Diazo Compounds Aryl Halides Arylboronic Acids
刊名SYNTHESIS-STUTTGART
2010-12-01
DOI10.1055/s-0030-1258322
24页:4154-4168
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology ; Physical Sciences
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]N-HETEROCYCLIC CARBENES ; BETA-HYDRIDE ELIMINATION ; ORGANIC-SYNTHESIS ; ASYMMETRIC CYCLOPROPANATION ; STEREOSELECTIVE-SYNTHESIS ; MIGRATORY INSERTION ; ARYL HALIDES ; MEDIATED COPOLYMERIZATION ; CARBONYLATION REACTIONS ; STABILIZED CARBENE
英文摘要Efficient palladium-catalyzed cross-coupling reactions of alpha-diazocarbonyl compounds and arylboronic acids or aryl halides have been developed. The reaction proceeds smoothly for a range of diazo compounds, boronic acids, and halides. The coupling reaction conditions tolerate various substituents on the aromatic rings of the substrates, such as chloro, fluoro, acyl, oxo, ester, and nitro groups. This coupling reaction constitutes a novel access to alpha-aryl-substituted alpha,beta-unsaturated carbonyl compounds. Mechanistically, palladium-carbene is supposed to be the key intermediate; its formation is followed by migratory insertion of an aryl group to the carbenic carbon of the palladium-carbene complex and subsequent beta-hydride elimination. Kinetic isotope effect (KIE) data measured for intra- and intermolecular competition experiments suggest that beta-hydride elimination is not involved in the rate-determining step.
语种英语
WOS记录号WOS:000286479200002
引用统计
被引频次:23[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/141875
专题中国科学院大连化学物理研究所
作者单位Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China
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GB/T 7714
Peng, Cheng,Yan, Guobin,Wang, Yan,et al. Palladium-Catalyzed Coupling Reaction of alpha-Diazocarbonyl Compounds with Aromatic Boronic Acids or Halides[J]. SYNTHESIS-STUTTGART,2010(24):4154-4168.
APA Peng, Cheng,Yan, Guobin,Wang, Yan,Jiang, Yubo,Zhang, Yan,&Wang, Jianbo.(2010).Palladium-Catalyzed Coupling Reaction of alpha-Diazocarbonyl Compounds with Aromatic Boronic Acids or Halides.SYNTHESIS-STUTTGART(24),4154-4168.
MLA Peng, Cheng,et al."Palladium-Catalyzed Coupling Reaction of alpha-Diazocarbonyl Compounds with Aromatic Boronic Acids or Halides".SYNTHESIS-STUTTGART .24(2010):4154-4168.
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