Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination
Type
ArticleAuthors
Moulin, SolenneDentel, Hélène
Pagnoux-Ozherelyeva, Anastassiya
Gaillard, Sylvain
Poater, Albert

Cavallo, Luigi

Lohier, Jean François
Renaud, Jean Luc
KAUST Department
Chemical Science ProgramKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2013-11-15Online Publication Date
2013-11-15Print Publication Date
2013-12-23Permanent link to this record
http://hdl.handle.net/10754/563086
Metadata
Show full item recordAbstract
Reductive amination under hydrogen pressure is a valuable process in organic chemistry to access amine derivatives from aldehydes or ketones. Knölker's complex has been shown to be an efficient iron catalyst in this reaction. To determine the influence of the substituents on the cyclopentadienone ancillary ligand, a series of modified Knölker's complexes was synthesised and fully characterised. These complexes were also transformed into their analogous acetonitrile iron-dicarbonyl complexes. Catalytic activities of these complexes were evaluated and compared in a model reaction. The scope of this reaction is also reported. For mechanistic insights, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Festival of amination: Two series of modified Knölker's complexes were synthesised and applied in the reductive amination of various carbonyl derivatives with primary or secondary amines (see scheme, TIPS = triisopropylsilyl). For a mechanistic insight, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.Citation
Moulin, S., Dentel, H., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2013). Bifunctional (Cyclopentadienone)Iron-Tricarbonyl Complexes: Synthesis, Computational Studies and Application in Reductive Amination. Chemistry - A European Journal, 19(52), 17881–17890. doi:10.1002/chem.201302432Sponsors
The authors declare no competing financial interest. The authors thank Oril Industries for a post-doc fellowship (S.M.). We gratefully acknowledge financial support from the "Ministere de la Recherche et des Nouvelles Technologies" for a PhD grant for A.P.O., CNRS (Centre National de la Recherche Scientifique), the "Region Basse-Normandie", the "CRUNCH" interregional network and the European Union (FEDER funding). A.P. thanks the Spanish MICINN for a Ramon y Cajal contract (RYC-2009-04170), the Generalitat de Catalunya (2012 BE100824) and the European Commission for a Career Integration Grant (CIG09-GA-2011-293900). The authors warmly thank Dr. Remi Legay for the NMR spectroscopic analysis.Publisher
WileyJournal
Chemistry - A European JournalRelations
Is Supplemented By:- [Dataset]
Dentel, H., Moulin, S., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2014). CCDC 910701: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczkngm. DOI: 10.5517/cczkngm HANDLE: 10754/624764 - [Dataset]
Dentel, H., Moulin, S., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2014). CCDC 910700: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczknfl. DOI: 10.5517/cczknfl HANDLE: 10754/624763 - [Dataset]
Dentel, H., Moulin, S., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2014). CCDC 910699: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczkndk. DOI: 10.5517/cczkndk HANDLE: 10754/624762 - [Dataset]
Dentel, H., Moulin, S., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2014). CCDC 910698: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczkncj. DOI: 10.5517/cczkncj HANDLE: 10754/624761 - [Dataset]
Dentel, H., Moulin, S., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2014). CCDC 910697: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczknbh. DOI: 10.5517/cczknbh HANDLE: 10754/624760 - [Dataset]
Dentel, H., Moulin, S., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2014). CCDC 910696: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczkn9g. DOI: 10.5517/cczkn9g HANDLE: 10754/624759 - [Dataset]
Dentel, H., Moulin, S., Pagnoux-Ozherelyeva, A., Gaillard, S., Poater, A., Cavallo, L., … Renaud, J.-L. (2014). CCDC 910695: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczkn8f. DOI: 10.5517/cczkn8f HANDLE: 10754/624758
ae974a485f413a2113503eed53cd6c53
10.1002/chem.201302432