Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination
dc.contributor.author
dc.date.accessioned
2015-05-04T10:21:14Z
dc.date.available
2015-05-04T10:21:14Z
dc.date.issued
2013-12-23
dc.identifier.issn
0947-6539
dc.identifier.uri
dc.description.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
dc.description.sponsorship
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.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
Wiley-VCH Verlag
dc.relation
info:eu-repo/grantAgreement/MICINN//RYC-2009-04170/ES/RYC-2009-04170/
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Reproducció digital del document publicat a: http://dx.doi.org/10.1002/chem.201302432
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© Chemistry - A European Journal, 2013, vol. 19, p. 17881-17890
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Articles publicats (D-Q)
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Tots els drets reservats
dc.subject
dc.title
Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/embargoedAccess
dc.embargo.terms
Cap
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2026-01-01
dc.relation.projectID
info:eu-repo/grantAgreement/EC/FP7/293900/EU/Ab initio Statics and Molecular Dynamics Simulation of Olefin Metathesis Catalysts for pharmacological purposes/COMPUTEDRUG
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
020509
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dc.relation.FundingProgramme
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dc.identifier.eissn
1521-3765