Rh-catalyzed sulfonic acid group directed ortho C-H olefination of arenes

被引：28
作者：
Dong, Yi [1 ,2 ]
Liu, Gang [1 ,2 ,3 ,4 ]
机构：
[1] Chinese Acad Med Sci, Inst Mat Med, Beijing 100050, Peoples R China
[2] Peking Union Med Coll, Beijing 100050, Peoples R China
[3] Tsinghua Univ, Tsinghua Peking Ctr Life Sci, Beijing 100084, Peoples R China
[4] Tsinghua Univ, Sch Med, Dept Pharmacol & Pharmaceut Sci, Beijing 100084, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 73期
基金：
中国国家自然科学基金;
关键词：
ORTHO-ALKENYLATION; BOND ACTIVATION; FUNCTIONALIZATION; VERSATILE; ALKENES; SELECTIVITY; INHIBITORS; REACTIVITY; SULTONES; SILANOL;
D O I：
10.1039/c3cc44690e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Rh-catalyzed ortho C-H olefination of arenes directed by a sulfonic acid group was developed with good yields and a broad reaction scope. Efficient performance of the catalyst caused this electron-poor aromatic C-H to be activated effectively and unactivated alkenes are also suitable for this reaction.
引用
收藏
页码：8066 / 8068
页数：3
相关论文
共 59 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   Ruthenium diacetate-catalysed oxidative alkenylation of C-H bonds in air: synthesis of alkenyl N-arylpyrazoles [J].
Arockiam, Percia B. ;
Fischmeister, Cedric ;
Bruneau, Christian ;
Dixneuf, Pierre H. .
GREEN CHEMISTRY, 2011, 13 (11) :3075-3078
[3]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[4]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587
[5]   Mechanistic Study of the Oxidative Coupling of Styrene with 2-Phenylpyridine Derivatives Catalyzed by Cationic Rhodium(III) via C-H Activation [J].
Brasse, Mikael ;
Campora, Juan ;
Ellman, Jonathan A. ;
Bergman, Robert G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (17) :6427-6430
[6]   Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].
Cai, Guixin ;
Fu, Ye ;
Li, Yizhou ;
Wan, Xiaobing ;
Shi, Zhangjie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673
[7]   Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group [J].
Chan, Li Yan ;
Kim, Sunggak ;
Ryu, Taekyu ;
Lee, Phil Ho .
CHEMICAL COMMUNICATIONS, 2013, 49 (41) :4682-4684
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].
Colby, Denise A. ;
Tsai, Andy S. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825
[10]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
123456