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

Solenne Moulin, Hélène Dentel, Anastassiya Pagnoux-Ozherelyeva, Sylvain Gaillard, Albert Poater, Luigi Cavallo, Jean François Lohier, Jean Luc Renaud

Research output: Contribution to journalArticlepeer-review

108 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)17881-17890
Number of pages10
JournalChemistry - A European Journal
Volume19
Issue number52
DOIs
StatePublished - Nov 15 2013

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.

ASJC Scopus subject areas

  • General Chemistry

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