An efficient copper-catalyzed N-arylation of amides: synthesis of N-arylacrylamides and 4-amido-N-phenylbenzamides

被引：28

作者：

Quan, Zheng-Jun ^{[1
,2
]}

Xia, Hai-Dong ^{[1
,2
]}

Zhang, Zhang ^{[1
,2
]}

Da, Yu-Xia ^{[1
,2
]}

Wang, Xi-Cun ^{[1
,2
]}

机构：

[1] Minist Educ, Key Lab Ecoenvironm Related Polymer Mat, Lanzhou 730070, Gansu, Peoples R China

[2] Northwest Normal Univ, Coll Chem & Chem Engn, Gansu Key Lab Polymer Mat, Lanzhou 730070, Gansu, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 39期

关键词：

Copper; N-Arylation; Amides; Aryl iodides; C-N cross-coupling; ARYL HALIDES; C-N; COUPLING REACTION; AMINO-ACID; NUCLEOPHILIC-SUBSTITUTION; AROMATIC-SUBSTITUTION; ULLMANN CONDENSATION; GOLDBERG REACTIONS; AMIDATION; AMINATION;

D O I：

10.1016/j.tet.2013.07.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-catalyzed intermolecular C-N bond-forming reactions between aryl iodides and amides are described using sodium ascorbate, which is both cheap and nontoxic, as the additive. A variety of functionalized amides including some practical, unique secondary amides, such as N-arylacrylamides and 4-amido-N-phenylbenzamides, which are difficult to obtain by the classical methods, are prepared. Furthermore, some tertiary amides are prepared by using copper thiophenecarboxylate. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：8368 / 8374

页数：7

共 60 条

[41]

Negwar M., 1994, ORGANIC CHEM DRUGS T

[42] MECHANISMS AND MODELS FOR COPPER MEDIATED NUCLEOPHILIC AROMATIC-SUBSTITUTION .2. A SINGLE CATALYTIC SPECIES FROM 3 DIFFERENT OXIDATION-STATES OF COPPER IN AN ULLMANN SYNTHESIS OF TRIARYLAMINES [J].