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

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    Type
    Article
    Authors
    Moulin, Solenne
    Dentel, Hélène
    Pagnoux-Ozherelyeva, Anastassiya
    Gaillard, Sylvain
    Poater, Albert cc
    Cavallo, Luigi cc
    Lohier, Jean François
    Renaud, Jean Luc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2013-11-15
    Online Publication Date
    2013-11-15
    Print Publication Date
    2013-12-23
    Permanent link to this record
    http://hdl.handle.net/10754/563086
    
    Metadata
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    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.
    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.201302432
    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.
    Publisher
    Wiley
    Journal
    Chemistry - A European Journal
    DOI
    10.1002/chem.201302432
    Relations
    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
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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