Tetrazole-1-acetic acid as a ligand for copper-catalyzed N-arylation of imidazoles with aryl iodides under mild conditions

被引:20
作者
Wu, Feng-Tian [1 ]
Liu, Ping [1 ]
Ma, Xiao-Wei [1 ]
Xie, Jian-Wei [1 ]
Dai, Bin [1 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832003, Peoples R China
关键词
Tetrazole-1-acetic acid; N-Arylation; Imidazoles; Copper; Aryl iodides; C-N; COUPLING REACTIONS; CRYSTAL-STRUCTURE; RECENT PROGRESS; POLYMERS; HALIDES; TZA;
D O I
10.1016/j.cclet.2013.05.037
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tetrazole-1-acetic acid was found to serve as a superior ligand for CuI-catalyzed N-arylation of imidazoles with aryl iodides under a low catalyst loading (5 mol% of CuI). A variety of aryl iodides could be aminated to provide the N-arylated products in good to excellent yields without the need of an inert atmosphere. (C) 2013 Jian-Wei Xie. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:893 / 896
页数:4
相关论文
共 21 条
[1]  
Antonini I., 1983, SYNTHESIS-STUTTGART, V1983, P47
[2]   CuI/PPh3/PEG-WATER: AN EFFICIENT CATALYTIC SYSTEM FOR CROSS-COUPLING REACTION OF ARYL IODIDES AND ALKYNES [J].
Chen, Gong ;
Xie, Jianwei ;
Weng, Jiang ;
Zhu, Xinhai ;
Zheng, Zhanchao ;
Cai, Jiwen ;
Wan, Yiqian .
SYNTHETIC COMMUNICATIONS, 2011, 41 (21) :3123-3133
[3]   Azole-Based Energetic Salts [J].
Gao, Haixiang ;
Shreeve, Jean'ne M. .
CHEMICAL REVIEWS, 2011, 111 (11) :7377-7436
[4]   A Simple and Efficient Copper(II) Complex as a Catalyst for N-Arylation of Imidazoles [J].
Jiao, Yanli ;
Yan, Nannan ;
Xie, Jianwei ;
Ma, Xiaowei ;
Liu, Ping ;
Dai, Bin .
CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (02) :267-270
[5]   Muscarine, imidazole, oxazole and thiazole alkaloids [J].
Jin, Z .
NATURAL PRODUCT REPORTS, 2005, 22 (02) :196-229
[6]   An efficient copper-catalyzed coupling of aryl halides with imidazoles [J].
Kiyomori, A ;
Marcoux, JF ;
Buchwald, SL .
TETRAHEDRON LETTERS, 1999, 40 (14) :2657-2660
[7]   A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles [J].
Klapars, A ;
Antilla, JC ;
Huang, XH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7727-7729
[8]   The chemistry of functionalised N-heterocyclic carbenes [J].
Kuhl, Olaf .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (04) :592-607
[9]   Progress in Copper-Catalyzed Ullmann-Type Coupling Reactions in Water [J].
Li, Zhengkai ;
Wu, Zhiqing ;
Deng, Hang ;
Zhou, Xiangge .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (04) :760-770
[10]   COPPER ASSISTED NUCLEOPHILIC-SUBSTITUTION OF ARYL HALOGEN [J].
LINDLEY, J .
TETRAHEDRON, 1984, 40 (09) :1433-1456