Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes

被引:120
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
    Allen, C. Liana
    Atkinson, Benjamin N.
    Williams, Jonathan M. J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (06) : 1383 - 1386
  • [2] Transamidation of primary amides with amines catalyzed by zirconocene dichloride
    Atkinson, Benjamin N.
    Chhatwal, A. Rosie
    Lomax, Helen V.
    Walton, James W.
    Williams, Jonathan M. J.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (95) : 11626 - 11628
  • [3] A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis
    Baker, Emma L.
    Yamano, Michael M.
    Zhou, Yujing
    Anthony, Sarah M.
    Garg, Neil K.
    [J]. NATURE COMMUNICATIONS, 2016, 7
  • [4] ALUMINUM CHLORIDE-PROMOTED TRANSAMIDATION REACTIONS
    BON, E
    BIGG, DCH
    BERTRAND, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4035 - 4036
  • [5] Analysis of the reactions used for the preparation of drug candidate molecules
    Carey, John S.
    Laffan, David
    Thomson, Colin
    Williams, Mike T.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) : 2337 - 2347
  • [6] Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes
    Cheung, Chi Wai
    Ploeger, Marten Leendert
    Hu, Xile
    [J]. CHEMICAL SCIENCE, 2018, 9 (03) : 655 - 659
  • [7] Nickel-Catalyzed Reductive Transamidation of Secondary Amides with Nitroarenes
    Cheung, Chi Wai
    Ploeger, Marten Leendert
    Hu, Xile
    [J]. ACS CATALYSIS, 2017, 7 (10): : 7092 - 7096
  • [8] Direct amidation of esters with nitroarenes
    Cheung, Chi Wai
    Ploeger, Marten Leendert
    Hu, Xile
    [J]. NATURE COMMUNICATIONS, 2017, 8
  • [9] Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides
    Cheung, Chi Wai
    Hu, Xile
    [J]. NATURE COMMUNICATIONS, 2016, 7
  • [10] Nickel-catalyzed transamidation of aliphatic amide derivatives
    Dander, Jacob E.
    Baker, Emma L.
    Garg, Neil K.
    [J]. CHEMICAL SCIENCE, 2017, 8 (09) : 6433 - 6438