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 [J].
Addis, Daniele ;
Shaikh, Nadim ;
Zhou, Shaolin ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthius .
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 [J].
Bedford, Robin B. ;
Hall, Mark A. ;
Hodges, George R. ;
Huwe, Michael ;
Wilkinson, Mark C. .
CHEMICAL COMMUNICATIONS, 2009, (42) :6430-6432
[6]   Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].
Beller, M ;
Seayad, J ;
Tillack, A ;
Jiao, H .
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 [J].
Boddien, Albert ;
Loges, Bjorn ;
Gaertner, Felix ;
Torborg, Christian ;
Fumino, Koichi ;
Junge, Henrik ;
Ludwig, Ralf ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) :8924-8934
[10]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254