Palladium-Catalyzed Coupling Reaction of alpha-Diazocarbonyl Compounds   with Aromatic Boronic Acids or Halides

doi:10.1055/s-0030-1258322

CORC > 北京大学 > 化学与分子工程学院

	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
刊名	synthesis stuttgart
	2010
关键词	palladium catalysis cross-coupling diazo compounds aryl halides arylboronic acids N-HETEROCYCLIC CARBENES BETA-HYDRIDE ELIMINATION ORGANIC-SYNTHESIS ASYMMETRIC CYCLOPROPANATION STEREOSELECTIVE-SYNTHESIS MIGRATORY INSERTION ARYL HALIDES MEDIATED COPOLYMERIZATION CARBONYLATION REACTIONS STABILIZED CARBENE
DOI	10.1055/s-0030-1258322
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.; Chemistry, Organic; SCI(E); 17; ARTICLE; 24; 4154-4168
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/395224]
专题	化学与分子工程学院
推荐引用方式 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.
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.
MLA	Peng, Cheng,et al."Palladium-Catalyzed Coupling Reaction of alpha-Diazocarbonyl Compounds with Aromatic Boronic Acids or Halides".synthesis stuttgart (2010).