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dc.contributor.authorMoulin, Solenne
dc.contributor.authorDentel, Hélène
dc.contributor.authorPagnoux-Ozherelyeva, Anastassiya
dc.contributor.authorGaillard, Sylvain
dc.contributor.authorPoater, Albert
dc.contributor.authorCavallo, Luigi
dc.contributor.authorLohier, Jean François
dc.contributor.authorRenaud, Jean Luc
dc.date.accessioned2015-08-03T11:35:27Z
dc.date.available2015-08-03T11:35:27Z
dc.date.issued2013-11-15
dc.identifier.issn09476539
dc.identifier.doi10.1002/chem.201302432
dc.identifier.urihttp://hdl.handle.net/10754/563086
dc.description.abstractReductive 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.
dc.description.sponsorshipThe 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.
dc.publisherWiley-Blackwell
dc.subjectamination
dc.subjectcatalysis
dc.subjectdensity functional calculations
dc.subjecthydrogenation
dc.subjectiron
dc.titleBifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination
dc.typeArticle
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Division
dc.contributor.departmentChemical Science Program
dc.identifier.journalChemistry - A European Journal
dc.contributor.institutionLaboratoire de Chimie Moléculaire et Thioorganique, Normandie University, UMR 6507, 6, Boulevard du Maréchal Juin, 14050 Caen, France
dc.contributor.institutionDepartament de Química, Institut de Química Computacional i Catàlisi (IQCC), University of Girona, 17071 Girona, Catalonia, Spain
kaust.personCavallo, Luigi
dc.relation.isSupplementedByDentel, 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
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dc.relation.isSupplementedByDentel, 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
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dc.relation.isSupplementedByDentel, 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
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dc.relation.isSupplementedByDentel, 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
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dc.relation.isSupplementedByDentel, 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
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dc.relation.isSupplementedByDentel, 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
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dc.relation.isSupplementedByDentel, 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
dc.relation.isSupplementedByDOI:10.5517/cczkn8f
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624758


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