Ligand-Controlled Para-Selective C-H Arylation of Monosubstituted Arenes

被引:38
作者
Xu, Hui [1 ]
Shang, Ming [1 ]
Dai, Hui-Xiong [1 ]
Yu, Jin-Quan [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
美国国家科学基金会; 中国博士后科学基金;
关键词
CATALYZED ORTHO-ARYLATION; ELECTRON-DEFICIENT ARENES; BOND ACTIVATION; COUPLING REACTIONS; UNACTIVATED ARENES; SODIUM PERSULFATE; C(SP(2))-H BONDS; COMPLEXES; FUNCTIONALIZATION; PD;
D O I
10.1021/acs.orglett.5b01802
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In a Pd-catalyzed double C-H activation reaction, a pyridine-type ligand is identified, for the first time, to enable a highly para-selective C-H arylation of monosubstituted arenes. Excellent para-selectivity is achieved with a variety of arenes containing alkyl, methoxyl, and halo substituents.
引用
收藏
页码:3830 / 3833
页数:4
相关论文
共 58 条
[41]   Angiotensin receptor blockers do not increase risk of myocardial infarction [J].
Tsuyuki, Ross T. ;
McDonald, Michael A. .
CIRCULATION, 2006, 114 (08) :855-860
[42]   Platinum-Catalyzed C-H Arylation of Simple Arenes [J].
Wagner, Anna M. ;
Hickman, Amanda J. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (42) :15710-15713
[43]   Highly selective C-H functionalization/halogenation of acetanilide [J].
Wan, Xiaobing ;
Ma, Zhongxun ;
Li, Bijie ;
Zhang, Keya ;
Cao, Shaokui ;
Zhang, Shiwei ;
Shi, Zhangjie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7416-7417
[44]   Ligand-enabled meta-C-H activation using a transient mediator [J].
Wang, Xiao-Chen ;
Gong, Wei ;
Fang, Li-Zhen ;
Zhu, Ru-Yi ;
Li, Suhua ;
Engle, Keary M. ;
Yu, Jin-Quan .
NATURE, 2015, 519 (7543) :334-338
[45]   Pd(II)-Catalyzed para-Selective C-H Arylation of Monosubstituted Arenes [J].
Wang, Xisheng ;
Leow, Dasheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) :13864-13867
[46]   Rhodium(III) and Hexabromobenzene-A Catalyst System for the Cross-Dehydrogenative Coupling of Simple Arenes and Heterocycles with Arenes Bearing Directing Groups [J].
Wencel-Delord, Joanna ;
Nimphius, Corinna ;
Wang, Honggen ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (52) :13001-13005
[47]   [RhIIICp*]-Catalyzed Dehydrogenative Aryl?Aryl Bond Formation [J].
Wencel-Delord, Joanna ;
Nimphius, Corinna ;
Patureau, Frederic W. ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) :2247-2251
[48]   Towards mild metal-catalyzed C-H bond activation [J].
Wencel-Delord, Joanna ;
Droege, Thomas ;
Liu, Fan ;
Glorius, Frank .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) :4740-4761
[49]   Palladium-Catalyzed Cross-Dehydrogenative Functionalization of C(sp2)-H Bonds [J].
Wu, Yinuo ;
Wang, Jun ;
Mao, Fei ;
Kwong, Fuk Yee .
CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) :26-47
[50]   Carbon-carbon bond formation through double Sp2 C-H activations:: Synthesis of ferrocenyl oxazoline derivatives [J].
Xia, Ji-Bao ;
You, Shu-Li .
ORGANOMETALLICS, 2007, 26 (20) :4869-4871