Palladium-catalyzed allene synthesis enabled by beta-hydrogen elimination from sp(2)-carbon

doi:10.1038/s41467-020-20740-w

	Palladium-catalyzed allene synthesis enabled by beta-hydrogen elimination from sp(2)-carbon
	Zhang, Ge1,2,3 ; Song, Yi-Kang 1; Zhang, Fang 1; Xue, Ze-Jian 2; Li, Meng-Yao 2; Zhang, Gui-Shan 2; Zhu, Bin-Bin 2; Wei, Jing 4; Li, Chunsen 4; Feng, Chen-Guo 1,2; Lin, Guo-Qiang1,2,3
	2021-02-01
发表期刊	NATURE COMMUNICATIONS (IF:14.7[JCR-2023],16.1[5-Year])
ISSN	2041-1723
卷号	12 期号:1 页码:#VALUE!
DOI	10.1038/s41467-020-20740-w
摘要	The rational design based on a deep understanding of the present reaction mechanism is an important, viable approach to discover new organic transformations. beta -Hydrogen elimination from palladium complexes is a fundamental reaction in palladium catalysis. Normally, the eliminated beta -hydrogen has to be attached to a sp(3)-carbon. We envision that the hydrogen elimination from sp(2)-carbon is possible by using thoroughly designed reaction systems, which may offer a new strategy for the preparation of allenes. Here, we describe a palladium-catalyzed cross-coupling of 2,2-diarylvinyl bromides and diazo compounds, where a beta -vinylic hydrogen elimination from allylic palladium intermediate is proposed to be the key step. Both aryl diazo carbonyl compounds and N-tosylhydrazones are competent carbene precursors in this reaction. The reaction mechanism is explored by control experiments, KIE studies and DFT calculations.beta -Hydrogen elimination is a fundamental reaction in palladium catalysis, however, the eliminated beta -hydrogen is usually attached to a sp(3)-carbon. Here, the authors report a palladium-catalyzed cross-coupling reaction involving a beta -vinylic hydrogen elimination from an allylic palladium intermediate.
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收录类别	SCI ; SCIE
语种	英语
WOS研究方向	Science & Technology - Other Topics
WOS类目	Multidisciplinary Sciences
WOS记录号	WOS:000616943800002
出版者	NATURE RESEARCH
原始文献类型	Article
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/125845
专题	物质科学与技术学院_博士生物质科学与技术学院_特聘教授组_林国强组
通讯作者	Wei, Jing; Feng, Chen-Guo; Lin, Guo-Qiang
作者单位	1.Shanghai Univ Tradit Chinese Med, Res Ctr Chiral Drugs, Innovat Res Inst Tradit Chinese Med, 1200 Cailun Rd, Shanghai 201203, Peoples R China; 2.Univ Chinese Acad Sci, Chinese Acad Sci, Ctr Excellence Mol Synth, CAS Key Lab Synthet Chem Nat Subst,Shanghai Inst, 345 Lingling Rd, Shanghai 200032, Peoples R China; 3.ShanghaiTech Univ, Sch Phys Sci & Technol, 393 Huaxia Rd, Shanghai 201210, Peoples R China; 4.Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, 155 West Yangqiao Rd, Fuzhou 350002, Peoples R China
第一作者单位	物质科学与技术学院
通讯作者单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Zhang, Ge,Song, Yi-Kang,Zhang, Fang,et al. Palladium-catalyzed allene synthesis enabled by beta-hydrogen elimination from sp(2)-carbon[J]. NATURE COMMUNICATIONS,2021,12(1):#VALUE!.
APA	Zhang, Ge.,Song, Yi-Kang.,Zhang, Fang.,Xue, Ze-Jian.,Li, Meng-Yao.,...&Lin, Guo-Qiang.(2021).Palladium-catalyzed allene synthesis enabled by beta-hydrogen elimination from sp(2)-carbon.NATURE COMMUNICATIONS,12(1),#VALUE!.
MLA	Zhang, Ge,et al."Palladium-catalyzed allene synthesis enabled by beta-hydrogen elimination from sp(2)-carbon".NATURE COMMUNICATIONS 12.1(2021):#VALUE!.