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

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 [Fe3(CO)12] and ligand...

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 50; no. 2; pp. 537 - 541
Main Authors Driller, Katrin Marie, Prateeptongkum, Saisuree, Jackstell, Ralf, Beller, Matthias
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 10.01.2011
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
acrylamides
Alkynes
carbonylation
Chemistry
Chemistry, Multidisciplinary
cinnamides
homogeneous catalysis
iron
Physical Sciences
Science & Technology
cinnamides
P-ARYLTHIO CINNAMIDES
EFFICIENT SYNTHESIS
TRANSFER HYDROGENATION
ALPHA,BETA-UNSATURATED AMIDES
CARBONYL-COMPLEXES
CROSS-COUPLING REACTIONS
homogeneous catalysis
acrylamides
iron
METAL
(E)-ALPHA,BETA-UNSATURATED AMIDES
carbonylation
ALLYLIC SUBSTITUTION
CYCLOBUTENEDIONES
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Summary: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 [Fe3(CO)12] and ligand L (see scheme). The method is highly chemo‐ and regioselective and requires no expensive catalyst.
Bibliography:http://dx.doi.org/10.1002/anie.201005823
ArticleID:ANIE201005823
Deutsche Forschungsgemeinschaft
This work was funded by the the Deutsche Forschungsgemeinschaft (Graduiertenkolleg 1213 and Leibniz-price). We thank Dr. C. Fischer, S. Buchholz, S. Schareina, A. Kammer, K. Fiedler, A. Lehmann, I. Stahr, A. Koch, and Dr. W. Baumann for their excellent technical and analytical support.
istex:1371A2AC20D2055E00EE2531F153CE3097AD0E10
ark:/67375/WNG-8QXMWW30-X
This work was funded by the the Deutsche Forschungsgemeinschaft (Graduiertenkolleg 1213 and Leibniz‐price). We thank Dr. C. Fischer, S. Buchholz, S. Schareina, A. Kammer, K. Fiedler, A. Lehmann, I. Stahr, A. Koch, and Dr. W. Baumann for their excellent technical and analytical support.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201005823