南方科技大学知识苑(SUSTech KC): Surface-Dependent Chemoselectivity in C-C Coupling Reactions

题名	Surface-Dependent Chemoselectivity in C-C Coupling Reactions
作者	Chen, Zhi 1,5; Lin, Tao 2,6; Zhang, Liding2,3 ; Zhang, Lei ; Xiang, Bingxi 6; Xu, Hu3 ; Klappenberger, Florian 2; Barth, Johannes V.2; Klyatskaya, Svetlana 1; Ruben, Mario 1,4
通讯作者	Chen, Zhi; Lin, Tao; Klappenberger, Florian; Ruben, Mario
发表日期	2019-06-17
DOI	10.1002/anie.201900636
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 影响因子和分区
ISSN	1433-7851
EISSN	1521-3773
卷号	58 期号:25页码:8356-8361
摘要	Surface-confined covalent coupling reactions of the linear compound 4-(but-3-en-1-ynyl)-4 '-ethynyl-1,1 '-biphenyl (1), which contains one alkyne and one enyne group on opposing ends, have been investigated using scanning tunneling microscopy (STM) and density functional theory (DFT) calculations. The reactions show a surface-dependent chemoselectivity: on Au(111), compound 1 preferentially yields cyclotrimerization products, while on Cu(111), a selective coupling between the enyne and alkyne groups is observed. Linear, V-shaped string formations combined with Y-shaped bifurcation motifs result in a random reticulation on the entire surface. DFT calculations show that the C-H...pi(delta-) transition state of the reaction between the deprotonated alkyne group and a nearby H-donor of the alkene group plays a key role in the mechanism and high chemoselectivity. This study highlights a concept that opens new avenues to the surface-confined synthesis of covalent carbon-based sp-sp(2) polymers.
关键词	alkenes alkynes chemoselectivity cross-coupling scanning tunneling microscopy
相关链接	[来源记录]
收录类别	SCI ; EI ; IC
语种	英语
重要成果	NI期刊
学校署名	其他
资助项目	Shenzhen Science and Technology Planning[JCYJ20170818143327496]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000476608700010
出版者	WILEY-V C H VERLAG GMBH
EI入藏号	20192106951444
EI主题词	Chemical bonds ; Density functional theory ; Group theory ; Olefins ; Scanning tunneling microscopy
EI分类号	Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1 ; Algebra:921.1 ; Probability Theory:922.1
ESI学科分类	CHEMISTRY
来源库	Web of Science
引用统计	被引频次[WOS]：12
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/25678
专题	理学院_物理系
作者单位	1.KIT, Inst Nanotechnol, D-76344 Eggenstein Leopoldshafen, Germany 2.TUM, Dept Phys E20, D-85748 Garching, Germany 3.Southern Univ Sci & Technol, Dept Phys, Shenzhen 518055, Peoples R China 4.Univ Strasbourg, CNRS, IPCMS, F-67034 Strasbourg, France 5.Shenzhen Univ, Coll Phys & Optoelect Engn, Minist Educ, Int Collaborat Lab 2D Mat Optoelect Sci & Technol, Shenzhen 518060, Peoples R China 6.Shenzhen Technol Univ, Coll New Mat & New Energies, Shenzhen 518118, Peoples R China
推荐引用方式 GB/T 7714	Chen, Zhi,Lin, Tao,Zhang, Liding,et al. Surface-Dependent Chemoselectivity in C-C Coupling Reactions[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019,58(25):8356-8361.
APA	Chen, Zhi.,Lin, Tao.,Zhang, Liding.,Zhang, Lei.,Xiang, Bingxi.,...&Ruben, Mario.(2019).Surface-Dependent Chemoselectivity in C-C Coupling Reactions.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,58(25),8356-8361.
MLA	Chen, Zhi,et al."Surface-Dependent Chemoselectivity in C-C Coupling Reactions".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58.25(2019):8356-8361.