Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination

Handle URI:
http://hdl.handle.net/10754/563086
Title:
Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination
Authors:
Moulin, Solenne; Dentel, Hélène; Pagnoux-Ozherelyeva, Anastassiya; Gaillard, Sylvain; Poater, Albert; Cavallo, Luigi ( 0000-0002-1398-338X ) ; Lohier, Jean François; Renaud, Jean Luc
Abstract:
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.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program
Publisher:
Wiley-Blackwell
Journal:
Chemistry - A European Journal
Issue Date:
15-Nov-2013
DOI:
10.1002/chem.201302432
Type:
Article
ISSN:
09476539
Sponsors:
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.
Is Supplemented By:
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:http://hdl.handle.net/10754/624764; 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:http://hdl.handle.net/10754/624763; 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:http://hdl.handle.net/10754/624762; 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:http://hdl.handle.net/10754/624761; 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:http://hdl.handle.net/10754/624760; 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:http://hdl.handle.net/10754/624759; 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:http://hdl.handle.net/10754/624758
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorMoulin, Solenneen
dc.contributor.authorDentel, Hélèneen
dc.contributor.authorPagnoux-Ozherelyeva, Anastassiyaen
dc.contributor.authorGaillard, Sylvainen
dc.contributor.authorPoater, Alberten
dc.contributor.authorCavallo, Luigien
dc.contributor.authorLohier, Jean Françoisen
dc.contributor.authorRenaud, Jean Lucen
dc.date.accessioned2015-08-03T11:35:27Zen
dc.date.available2015-08-03T11:35:27Zen
dc.date.issued2013-11-15en
dc.identifier.issn09476539en
dc.identifier.doi10.1002/chem.201302432en
dc.identifier.urihttp://hdl.handle.net/10754/563086en
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.en
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.en
dc.publisherWiley-Blackwellen
dc.subjectaminationen
dc.subjectcatalysisen
dc.subjectdensity functional calculationsen
dc.subjecthydrogenationen
dc.subjectironen
dc.titleBifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive aminationen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.identifier.journalChemistry - A European Journalen
dc.contributor.institutionLaboratoire de Chimie Moléculaire et Thioorganique, Normandie University, UMR 6507, 6, Boulevard du Maréchal Juin, 14050 Caen, Franceen
dc.contributor.institutionDepartament de Química, Institut de Química Computacional i Catàlisi (IQCC), University of Girona, 17071 Girona, Catalonia, Spainen
kaust.authorCavallo, Luigien
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/cczkngmen
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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/cczkndken
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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/cczkncjen
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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/cczknbhen
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