New ligands for copper-catalyzed C-N coupling reactions with aryl halides

被引:9
作者
Chen, Dong [1 ,2 ]
Yang, Kai [2 ]
Xiang, Hua [1 ]
Jiang, Sheng [2 ]
机构
[1] China Pharmaceut Univ, Coll Pharm, Dept Med Chem, Nanjing 210009, Peoples R China
[2] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Lab Regenerat Biol, Guangzhou 510530, Guangdong, Peoples R China
关键词
C-N coupling reactions; Copper; Cross-coupling; 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide; Ullmann reactions; PHOSPHINE OXIDE LIGAND; HIGHLY EFFICIENT; BOND FORMATION; ROOM-TEMPERATURE; AMINO-ACID; ARYLATION; BROMIDES; IODIDES; AMINATION; MILD;
D O I
10.1016/j.tetlet.2012.10.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-containing heterocycles under mild conditions. The catalytic system showed great functional-group tolerance and excellent chemoselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7121 / 7124
页数:4
相关论文
共 35 条
[21]   Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions [J].
Monnier, Florian ;
Taillefer, Marc .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :6954-6971
[22]   Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst [J].
Ntaganda, Rukundo ;
Dhudshia, Bhartesh ;
Macdonald, Charles L. B. ;
Thadani, Avinash N. .
CHEMICAL COMMUNICATIONS, 2008, (46) :6200-6202
[23]   New Ligands That Promote Cross-Coupling Reactions between Aryl Halides and Unactivated Arenes [J].
Qiu, Yatao ;
Liu, Yanhan ;
Yang, Kai ;
Hong, Wenkun ;
Li, Zheng ;
Wang, Zhaoyang ;
Yao, Zhiyi ;
Jiang, Sheng .
ORGANIC LETTERS, 2011, 13 (14) :3556-3559
[24]   A versatile and efficient ligand for copper-catalyzed formation of C-N, C-o, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester [J].
Rao, HH ;
Jin, Y ;
Fu, H ;
Jiang, YY ;
Zhao, YF .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) :3636-3646
[25]   N- versus O-arylation of aminoalcohols: Orthogonal selectivity in copper-based catalysts [J].
Shafir, Alexandr ;
Lichtor, Phillip A. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (12) :3490-+
[26]   Highly selective room-temperature copper-catalyzed C-N coupling reactions [J].
Shafir, Alexandr ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) :8742-8743
[27]   Per-6-amino-β-cyclodextrin as an Efficient Supramolecular Ligand and Host for Cu(I)-Catalyzed N-Arylation of Imidazole with Aryl Bromides [J].
Suresh, Palaniswamy ;
Pitchumani, Kasi .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :9121-9124
[28]   1,2,3,4-Tetrahydro-8-hydroxyquinoline-Promoted Copper-Catalyzed Coupling of Nitrogen Nucleophiles and Aryl Bromides [J].
Wang, Huifeng ;
Li, Yaming ;
Sun, Fangfang ;
Feng, Yang ;
Jin, Kun ;
Wang, Xiuna .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8639-8642
[29]   A Very Simple Copper-Catalyzed Synthesis of Anilines by Employing Aqueous Ammonia [J].
Xia, Ning ;
Taillefer, Marc .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (02) :337-339
[30]   Mild and efficient copper-catalyzed N-arylation of alkylamines and N-H heterocycles using an oxime-phosphine oxide ligand [J].
Xu, L ;
Zhu, D ;
Wu, F ;
Wang, RL ;
Wan, BS .
TETRAHEDRON, 2005, 61 (27) :6553-6560