Electrochemical N-acylation synthesis of amides under aqueous conditions

被引：44
作者：
Ke, Fang [1 ]
Xu, Yiwen [1 ]
Zhu, Suning [1 ]
Lin, Xiaoyan [1 ]
Lin, Chen [1 ]
Zhou, Sunying [1 ]
Su, Huimin [1 ]
机构：
[1] Fujian Med Univ, Inst Materia Med, Sch Pharm, Fujian Prov Key Lab Nat Med Pharmacol, Fuzhou 350122, Fujian, Peoples R China
来源：
GREEN CHEMISTRY | 2019年 / 21卷 / 16期
关键词：
CHEMISTRY RESEARCH AREAS; CARBOXYLIC-ACIDS; COUPLING REAGENTS; DIRECT AMIDATION; BOND FORMATION; SUBSTITUTION; PERSPECTIVE; ANTICANCER; CATALYST; CASCADE;
D O I：
10.1039/c9gc01391a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An electrochemical N-acylation of carboxylic acids with amines was reported. The sustainable TBAB electrocatalysis proceeded with excellent chemoselectivity and positional selectivity, and with ample scope, allowing electrochemical N-acylation under mild reaction conditions at room temperature in water. Moreover, the synthetic utility of the current method is demonstrated by the synthesis of melatonin.
引用
收藏
页码：4329 / 4333
页数：5
相关论文
共 54 条
[11]   Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].
Constable, David J. C. ;
Dunn, Peter J. ;
Hayler, John D. ;
Humphrey, Guy R. ;
Leazer, Johnnie L., Jr. ;
Linderman, Russell J. ;
Lorenz, Kurt ;
Manley, Julie ;
Pearlman, Bruce A. ;
Wells, Andrew ;
Zaks, Aleksey ;
Zhang, Tony Y. .
GREEN CHEMISTRY, 2007, 9 (05) :411-420
[12]  
Crisp G. T., 1998, TETRAHEDRON, V54, P679
[13]   Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines [J].
Denis, Jean-Baptiste ;
Masson, Geraldine ;
Retailleau, Pascal ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) :5356-5360
[14]   Organoboron Acids and Their Derivatives as Catalysts for Organic Synthesis [J].
Dimitrijevic, Elena ;
Taylor, Mark S. .
ACS CATALYSIS, 2013, 3 (05) :945-962
[15]   Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals [J].
Dunetz, Joshua R. ;
Magano, Javier ;
Weisenburger, Gerald A. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (02) :140-177
[16]   Peptide Coupling Reagents, More than a Letter Soup [J].
El-Faham, Ayman ;
Albericio, Fernando .
CHEMICAL REVIEWS, 2011, 111 (11) :6557-6602
[17]  
Gooβen L.J., 2009, SYNTHESIS, V1, P160
[18]   Intensified Azeotropic Distillation: A Strategy for Optimizing Direct Amidation [J].
Grosjean, Christophe ;
Parker, Julie ;
Thirsk, Carl ;
Wright, Allen R. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (05) :781-787
[19]  
Hanand S. Y., 2004, TETRAHEDRON, V60, P2447
[20]   Electrochemically induced free-radical tandem cyclisation of chlorodifluoromethylated ketones Application to the synthesis of gem-difluorinated heterocycles [J].
Hapiot, P ;
Médebielle, M .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (02) :285-300
123456