A General and Selective Iron-Catalyzed Aminocarbonylation of Alkynes: Synthesis of Acryl- and Cinnamides

被引:102
作者
Driller, Katrin Marie [1 ]
Prateeptongkum, Saisuree [1 ]
Jackstell, Ralf [1 ]
Beller, Matthias [1 ]
机构
[1] Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
acrylamides; carbonylation; cinnamides; homogeneous catalysis; iron; CROSS-COUPLING REACTIONS; P-ARYLTHIO CINNAMIDES; EFFICIENT SYNTHESIS; ALPHA; BETA-UNSATURATED AMIDES; CARBONYL-COMPLEXES; (E)-ALPHA; TRANSFER HYDROGENATION; ALLYLIC SUBSTITUTION; CYCLOBUTENEDIONES; METAL;
D O I
10.1002/anie.201005823
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Entering the iron age: The first general method for iron-catalyzed monocarbonylation of alkynes has been developed. A range of structurally diverse cinnamides and acrylamides have been obtained smoothly starting from commercially available amines and alkynes in the presence of [Fe 3(CO)12] and ligand L (see scheme). The method is highly chemo- and regioselective and requires no expensive catalyst. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:537 / 541
页数:5
相关论文
共 120 条
  • [1] Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones
    Addis, Daniele
    Shaikh, Nadim
    Zhou, Shaolin
    Das, Shoubhik
    Junge, Kathrin
    Beller, Matthius
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) : 1687 - 1691
  • [2] [Anonymous], ANGEW CHEM
  • [3] [Anonymous], 2009, ANGEW CHEM
  • [4] [Anonymous], 2009, ANGEW CHEM
  • [5] Simple mixed Fe-Zn catalysts for the Suzuki couplings of tetraarylborates with benzyl halides and 2-halopyridines
    Bedford, Robin B.
    Hall, Mark A.
    Hodges, George R.
    Huwe, Michael
    Wilkinson, Mark C.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (42) : 6430 - 6432
  • [6] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends
    Beller, M
    Seayad, J
    Tillack, A
    Jiao, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) : 3368 - 3398
  • [7] Beller M, 2006, TOP ORGANOMETAL CHEM, V18, P1, DOI 10.1007/b105253
  • [8] Beller M, 2004, ANGEW CHEM, V116, P3448
  • [9] Iron-Catalyzed Hydrogen Production from Formic Acid
    Boddien, Albert
    Loges, Bjorn
    Gaertner, Felix
    Torborg, Christian
    Fumino, Koichi
    Junge, Henrik
    Ludwig, Ralf
    Beller, Matthias
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 8924 - 8934
  • [10] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254