Copper-Catalyzed N-Arylations of Nitrogen-Containing Heterocycles in Water

被引：18

作者：

Zhang, Jingxian ^{[1
]}

Yin, Huiqing ^{[1
]}

Han, Shiqing ^{[1
]}

机构：

[1] Nanjing Univ Technol, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Jiangsu, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 32卷 / 08期

基金：

中国国家自然科学基金;

关键词：

copper-catalyst; nitrogen-containing heterocycles; N-arylation; aqueous media; ARYL HALIDES; COUPLING REACTION; ARYLBORONIC ACIDS; BOND FORMATION; AMINO-ACID; EFFICIENT; IMIDAZOLES; LIGANDS;

D O I：

10.6023/cjoc201205018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, efficient, inexpensive and powerful method for the C-N coupling of nitrogen-containing heterocycles with aryl halides was developed by using cheap Cu2O as catalyst, inexpensive and readily available 8-hydroxyquinoline as ligand, n-Bu4NBr as phase transfer catalyst, water as solvent at 100 degrees C. Most products were synthesized in good to excellent yields.

引用

收藏

页码：1429 / 1433

页数：5

相关论文

共 25 条

[1] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[2] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[3] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[4] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].

Collman, JP ;

Zhong, M .

ORGANIC LETTERS, 2000, 2 (09) :1233-1236

[5] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[6] Iron-catalyzed N-arylation of nitrogen nucleophiles [J].

Correa, Arkaitz ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8862-8865

[7] A Facile and Practical Copper Powder-Catalyzed, Organic Solvent- and Ligand-Free Ullmann Amination of Aryl Halides [J].

Jiao, Jiao ;

Zhang, Xi-Ru ;

Chang, Ning-Hui ;

Wang, Jie ;

Wei, Jun-Fa ;

Shi, Xian-Ying ;

Chen, Zhan-Guo .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (04) :1180-1183

[8] An efficient base-free N-arylation of imidazoles and amines with arylboronic acids using copper-exchanged fluorapatite [J].

Kantam, M. Lakshmi ;

Venkanna, Gopaldasu T. ;

Sridhar, Chidara ;

Sreedhar, Bojja ;

Choudary, Boyapati M. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9522-9524

[9] An efficient copper-catalyzed coupling of aryl halides with imidazoles [J].

Kiyomori, A ;

Marcoux, JF ;

Buchwald, SL .

TETRAHEDRON LETTERS, 1999, 40 (14) :2657-2660

[10] 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