Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes

被引:123
作者
Cheung, Chi Wai [1 ,2 ,3 ]
Ma, Jun-An [2 ,3 ]
Hu, Xile [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Inorgan Synth & Catalysis, ISIC LSCI,BCH 3305, CH-1015 Lausanne, Switzerland
[2] Tianjin Univ, Tianjin Key Lab Mol Optoelect Sci, Dept Chem, Tianjin 300072, Peoples R China
[3] Tianjin Univ, Tianjin Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED TRANSAMIDATION; SECONDARY AMIDES; PRIMARY CARBOXAMIDES; DIRECT AMIDATION; UREAS; ACID;
D O I
10.1021/jacs.8b03739
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Amides are an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamidation. Here we describe an unconventional approach to the transamidation of tertiary amides using nitroarenes as the nitrogen source under reductive conditions. Manganese metal alone mediates the reactions and no additional catalyst is required. The method exhibits broad scope and high functional group tolerance.
引用
收藏
页码:6789 / 6792
页数:4
相关论文
共 26 条
[1]   Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst [J].
Allen, C. Liana ;
Atkinson, Benjamin N. ;
Williams, Jonathan M. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (06) :1383-1386
[2]   Transamidation of primary amides with amines catalyzed by zirconocene dichloride [J].
Atkinson, Benjamin N. ;
Chhatwal, A. Rosie ;
Lomax, Helen V. ;
Walton, James W. ;
Williams, Jonathan M. J. .
CHEMICAL COMMUNICATIONS, 2012, 48 (95) :11626-11628
[3]   A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis [J].
Baker, Emma L. ;
Yamano, Michael M. ;
Zhou, Yujing ;
Anthony, Sarah M. ;
Garg, Neil K. .
NATURE COMMUNICATIONS, 2016, 7
[4]   ALUMINUM CHLORIDE-PROMOTED TRANSAMIDATION REACTIONS [J].
BON, E ;
BIGG, DCH ;
BERTRAND, G .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4035-4036
[5]   Analysis of the reactions used for the preparation of drug candidate molecules [J].
Carey, John S. ;
Laffan, David ;
Thomson, Colin ;
Williams, Mike T. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347
[6]   Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes [J].
Cheung, Chi Wai ;
Ploeger, Marten Leendert ;
Hu, Xile .
CHEMICAL SCIENCE, 2018, 9 (03) :655-659
[7]   Nickel-Catalyzed Reductive Transamidation of Secondary Amides with Nitroarenes [J].
Cheung, Chi Wai ;
Ploeger, Marten Leendert ;
Hu, Xile .
ACS CATALYSIS, 2017, 7 (10) :7092-7096
[8]   Direct amidation of esters with nitroarenes [J].
Cheung, Chi Wai ;
Ploeger, Marten Leendert ;
Hu, Xile .
NATURE COMMUNICATIONS, 2017, 8
[9]   Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides [J].
Cheung, Chi Wai ;
Hu, Xile .
NATURE COMMUNICATIONS, 2016, 7
[10]   Nickel-catalyzed transamidation of aliphatic amide derivatives [J].
Dander, Jacob E. ;
Baker, Emma L. ;
Garg, Neil K. .
CHEMICAL SCIENCE, 2017, 8 (09) :6433-6438