Copper-catalyzed synthesis of primary arylamines via cascade reactions of aryl halides with amidine hydrochlorides

被引：79

作者：

Gao, Xiaoting ^{[1
,2
]}

Fu, Hua ^{[1
]}

Qiao, Renzhong ^{[2
]}

Jiang, Yuyang ^{[1
,3
]}

Zhao, Yufen ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China

[2] Beijing Univ Chem Technol, Dept Pharmaceut Engn, Coll Life Sci & Technol, Beijing 100029, Peoples R China

[3] Tsinghua Univ, Key Lab Chem Biol Guangdong Prov, Grad Sch, Shenzhen 518057, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 17期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/jo800818e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an efficient method for the synthesis of primary arylamines from aryl halides using amidine hydrochlorides as the ammonia surrogates. The protocol uses 10 mol % CuI as the catalyst, 20 mol % L-proline as the ligand, CS2CO3 as the base, and DMF as the solvent and proceeds the sequential coupling of aryl halides with amidine hydrochlorides and hydrolysis of intermediates to give the target products. This is a convenient, inexpensive, and practical approach to primary arylamines.

引用

页码：6864 / 6866

页数：3

共 73 条

[1] Mechanistic studies of the palladium-catalyzed amination of aryl halides and the oxidative addition of aryl bromides to Pd(BINAP)2 and Pd(DPPF)2:: An unusual case of zero-order kinetic behavior and product inhibition [J].