Copper-catalyzed ortho-halogenation of arenes and heteroarenes directed by a removable auxiliary

被引:89
作者
Li, Bo [1 ]
Liu, Bin [1 ]
Shi, Bing-Feng [1 ,2 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
关键词
C-H BONDS; CROSS-COUPLING REACTIONS; CARBON-HYDROGEN BONDS; OXIDATIVE FUNCTIONALIZATION; KINETIC RESOLUTION; C(SP(3))-H BONDS; PALLADIUM; IODINATION; ACTIVATION; HALIDES;
D O I
10.1039/c5cc00531k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Copper-catalyzed ortho-halogenation of C(sp(2))-H bonds directed by a PIP directing group with NXS (X = Cl, Br, I) has been developed. The reaction is scalable and tolerates a broad range of functional groups and heteroarenes, providing an efficient access to halogenated arenes and heteroarenes.
引用
收藏
页码:5093 / 5096
页数:4
相关论文
共 62 条
[41]   Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 Carbon-Hydrogen Bonds [J].
Shabashov, Dmitry ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3965-3972
[42]   DIRECTED ORTHO METALATION - TERTIARY AMIDE AND O-CARBAMATE DIRECTORS IN SYNTHETIC STRATEGIES FOR POLYSUBSTITUTED AROMATICS [J].
SNIECKUS, V .
CHEMICAL REVIEWS, 1990, 90 (06) :879-933
[43]   Palladium-Catalyzed Monoselective Halogenation of C-H Bonds: Efficient Access to Halogenated Arylpyrimidines using Calcium Halides [J].
Song, Bingrui ;
Zheng, Xiaojian ;
Mo, Jun ;
Xu, Bin .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) :329-335
[44]   Divergence between Organometallic and Single-Electron-Transfer Mechanisms in Copper(II)-Mediated Aerobic C-H Oxidation [J].
Suess, Alison M. ;
Ertem, Mehmed Z. ;
Cramer, Christopher J. ;
Stahl, Shannon S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (26) :9797-9804
[45]   Copper-catalyzed ortho-halogenation of protected anilines [J].
Urones, Beatriz ;
Manu Martinez, Angel ;
Rodriguez, Nuria ;
Gomez Arrayas, Ramon ;
Carretero, Juan C. .
CHEMICAL COMMUNICATIONS, 2013, 49 (94) :11044-11046
[46]   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
[47]   Ruthenium-catalyzed ortho-C-H halogenations of benzamides [J].
Wang, Lianhui ;
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2014, 50 (09) :1083-1085
[48]   Copper(II)-catalyzed ortho-functionalization of 2-arylpyridines with acyl chlorides [J].
Wang, Wenhui ;
Pan, Changduo ;
Chen, Fan ;
Cheng, Jiang .
CHEMICAL COMMUNICATIONS, 2011, 47 (13) :3978-3980
[49]   Pd(II)-Catalyzed C-H Iodination Using Molecular I2 as the Sole Oxidant [J].
Wang, Xiao-Chen ;
Hu, Yi ;
Bonacorsi, Samuel ;
Hong, Yang ;
Burrell, Richard ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (28) :10326-10329
[50]   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