Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides

被引:116
作者
Verma, Akhilesh Kumar [1 ]
Singh, Jaspal [1 ]
Sankar, V. Kasi [1 ]
Chaudhary, Ritu [1 ]
Chandra, Ramesh [1 ]
机构
[1] Univ Delhi, Synthet Organ Chem Res Lab, Dr BR Ambedkar Ctr Biomed Res, Delhi 110007, India
关键词
benzotriazole; CuI; N-arylation; imidazoles;
D O I
10.1016/j.tetlet.2007.04.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzotriazole (BtH) is an efficient ligand for the Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides. A combination of CuI/BtH was found to be an efficient and inexpensive catalyst system to carry out the N-arylation of imidazoles affording the corresponding products in good to excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4207 / 4210
页数:4
相关论文
共 56 条
[51]   2-aminopyrimidine-4,6-diol as an efficient ligand for solvent-free copper-catalyzed N-arylations of imidazoles with aryl and heteroaryl halides [J].
Xie, Ye-Xiang ;
Pi, Shao-Feng ;
Wang, Jian ;
Yin, Lin ;
Li, Jin-Heng .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :8324-8327
[52]   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
[53]   Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles [J].
Zhang, H ;
Cai, Q ;
Ma, DW .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5164-5173
[54]   Ambient temperature, Ullmann-like reductive coupling of aryl, heteroaryl, and alkenyl halides [J].
Zhang, SJ ;
Zhang, DW ;
Liebeskind, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2312-2313
[55]   Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles [J].
Zhang, ZJ ;
Mao, JC ;
Zhu, D ;
Wu, F ;
Chen, HL ;
Wan, BS .
TETRAHEDRON, 2006, 62 (18) :4435-4443
[56]   A QSAR study on inhibitory activities of 1-phenylbenzimidazoles against the platelet-derived growth factor receptor [J].
Zhong, CL ;
He, JT ;
Xue, CY ;
Li, YJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) :4009-4015