Mechanistic Study on Pd/Mono-N-protected Amino Acid Catalyzed   Vinyl-Vinyl Coupling Reactions: Reactivity and E/Z Selectivity

doi:10.1021/acs.orglett.6b02542

CORC > 北京大学 > 化学与分子工程学院

	Mechanistic Study on Pd/Mono-N-protected Amino Acid Catalyzed Vinyl-Vinyl Coupling Reactions: Reactivity and E/Z Selectivity
	Zhong, Xiu-Mei ; Cheng, Gui-Juan ; Chen, Ping ; Zhang, Xinhao ; Wu, Yun-Dong
刊名	ORGANIC LETTERS
	2016
关键词	C-H ACTIVATION BOND ACTIVATION GAS-PHASE ELECTROSPRAY-IONIZATION LINEAR 1,3-BUTADIENES SIMPLE ALKENES EFFICIENT ACRYLATES PD ALKENYLATION
DOI	10.1021/acs.orglett.6b02542
英文摘要	A combined mass spectrometric and computational study of the Pd/mono-N-protected amino acid (MPAA)-catalyzed vinyl-vinyl coupling reactions is reported. Computational study reveals that the reaction is initiated by C-H activation of the styrene followed by the insertion of acrylate. This is supported by mass spectrometry. The MPAA ligand facilitates the cross-coupling reaction between monosubstituted alkenes by stabilizing the active palladium catalyst and offering the N-protecting group as a stronger base than acetate. The E/Z selectivity is attributed to the stronger d-pi interaction between the catalyst and the substrate in the transition state leading to E product.; National Natural Science Foundation of China [21133002, 21232001, 21302006]; MOST of China [2013CB911501]; Shenzhen STIC [KQTD201103, JCYJ20140509093817689]; SCI(E); PubMed; ARTICLE; zhangxh@pkusz.edu.cn; wuyd@pkusz.edu.cn; 20; 5240-5243; 18
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/492602]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Zhong, Xiu-Mei,Cheng, Gui-Juan,Chen, Ping,et al. Mechanistic Study on Pd/Mono-N-protected Amino Acid Catalyzed Vinyl-Vinyl Coupling Reactions: Reactivity and E/Z Selectivity[J]. ORGANIC LETTERS,2016.
APA	Zhong, Xiu-Mei,Cheng, Gui-Juan,Chen, Ping,Zhang, Xinhao,&Wu, Yun-Dong.(2016).Mechanistic Study on Pd/Mono-N-protected Amino Acid Catalyzed Vinyl-Vinyl Coupling Reactions: Reactivity and E/Z Selectivity.ORGANIC LETTERS.
MLA	Zhong, Xiu-Mei,et al."Mechanistic Study on Pd/Mono-N-protected Amino Acid Catalyzed Vinyl-Vinyl Coupling Reactions: Reactivity and E/Z Selectivity".ORGANIC LETTERS (2016).