Optimization of the conditions for copper-mediated N-arylation of heteroarylamines

被引：61

作者：

Liu, Yifeng ^{[1
]}

Bai, Yajun ^{[1
]}

Zhang, Juan ^{[1
]}

Li, Yangyang ^{[2
]}

Jiao, Junping ^{[1
]}

Qi, Xiaoli ^{[1
]}

机构：

[1] NW Univ Xian, Inst Appl Chem, Xian 710069, Peoples R China

[2] Publ Bureau Xian, Technol Off Criminal Detect Bureau, Xian 710016, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 36期

关键词：

amines; aryl halides; arylation; copper;

D O I：

10.1002/ejoc.200700577

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Simple and inexpensive copper-mediated N-arylation of heteroarylamines was achieved by using N,N'-dimethylethylenediamine as a ligand and K2CO3 as a base in dioxane heated at 100 degrees C. In this coupling reaction, the influence of the copper species, ligand, base and solvent was investigated in detail. N-Arylated derivatives of several heteroarylamines were synthesized under optimized reaction conditions, and all the products were isolated in good yields. By controlling the amount of CuI/DMEDA added, heteroarylamines with weak nucleophilic activity were coupled with aryl iodides or aryl bromides. The activity of the copper catalyst for this C-N bond-forming reaction follows the order Cu-I>Cu-0>Cu-II. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007.

引用

页码：6084 / 6088

页数：5

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