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
[11]   A new iron age [J].
Bolm, Carsten .
NATURE CHEMISTRY, 2009, 1 (05) :420-420
[12]   Palladium-Catalyzed Carbonylation Reactions of Alkenes and Alkynes [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
CHEMCATCHEM, 2009, 1 (01) :28-41
[13]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[14]   Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity [J].
Bressi, Jerome C. ;
de Jong, Ron ;
Wu, Yiqin ;
Jennings, Andy J. ;
Brown, Jason W. ;
O'Connell, Shawn ;
Tari, Leslie W. ;
Skene, Robert J. ;
Vu, Phong ;
Navre, Marc ;
Cao, Xiaodong ;
Gangloff, Anthony R. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (10) :3138-3141
[15]   Comparing structures and reactivity in analogous Fe and Ru complexes.: (iPr-DAB)Fe(CO)2I2 and (iPr-DAB)FeI2:: a perfectly reversible CO-carrier system.: (R-DAB = N,N′-R2-1,4-diara-1,3-butadiene) [J].
Breuer, J ;
Frühauf, HW ;
Smeets, WJJ ;
Spek, AL .
INORGANICA CHIMICA ACTA, 1999, 291 (1-2) :438-447
[16]   On the Role of Metal Contaminants in Catalyses with FeCl3 [J].
Buchwald, Stephen L. ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587
[17]   An iron catalyst for ketone hydrogenations under mild conditions [J].
Bullock, R. Morris .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) :7360-7363
[18]   Some aspects of the properties and degradation of polyacrylamides [J].
Caulfield, MJ ;
Qiao, GG ;
Solomon, DH .
CHEMICAL REVIEWS, 2002, 102 (09) :3067-3083
[19]  
Colquhoun H.M., 1991, Carbonylation, Direct Synthesis of Carbonyl Compounds
[20]   Synthesis of aliphatic (E)-α,β-unsaturated amides with high diastereoselectivity from α,β-epoxyamides promoted by SmI2/HMPA [J].
Concellón, JM ;
Bardales, E .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (07) :1523-1526