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Catalysis Letters

, Volume 141, Issue 6, pp 808–816 | Cite as

Rhodium complexes containing chiral P-donor ligands as catalysts for asymmetric hydrogenation in non conventional media

  • Martha V. Escárcega-Bobadilla
  • Laura Rodríguez-Pérez
  • Emmanuelle Teuma
  • Philippe Serp
  • Anna M. Masdeu-BultóEmail author
  • Montserrat GómezEmail author
Article

Abstract

Rhodium-catalysed asymmetric hydrogenation using P-donor ligands, such as new fluorinated (R)-BINOL and azadioxaphosphabicyclo[3.3.0]octane derivatives was carried out in different reaction media such as organic solvent (CH2Cl2), ionic liquid ([BMI][PF6]), supercritical carbon dioxide (scCO2) and [BMI][PF6]/scCO2 mixture. The best enantioselectivities were obtained in neat [BMI][PF6], allowing a recycling up to ten times without activity loss. However, the enantioselectivity was lost due to ligand leaching. The ionic liquid phase containing rhodium molecular species was supported on functionalized multi-walled carbon nanotubes in order to improve the recycling, but unfortunately the asymmetric induction was lost upon catalyst immobilization.

Graphical Abstract

Rh-catalysed asymmetric hydrogenation was carried out in different reaction media (dichloromethane, scCO2, [BMI][PF6] and the mixture of scCO2/[BMI][PF6]) using chiral P-donor ligands under soft conditions. The best catalytic system was obtained in ionic liquid medium and could be recycled up to ten times without activity loss. The ionic liquid catalytic phase supported on functionalized multi-walled carbon nanotubes did not improve its catalytic behaviour.

Keywords

Asymmetric hydrogenation Rhodium Chiral monodentate P-donor ligands Ionic liquids Supercritical CO2 

Notes

Acknowledgements

We gratefully acknowledge C. Pradel for TEM analysis and the financial support of the CNRS, the Université Paul Sabatier, the Ministerio de Ciencia e Innovación (CTQ2007-63510PPQ and CSD2006-0003) and Generalitat de Catalunya (CTP 2007ITT-00007). M.V. Escárcega-Bobadilla thanks Generalitat de Catalunya, European Social Fund and Ministerio de Ciencia e Innovación for a predoctoral fellowship (FI, BE2008).

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Martha V. Escárcega-Bobadilla
    • 1
    • 2
  • Laura Rodríguez-Pérez
    • 1
    • 3
  • Emmanuelle Teuma
    • 1
  • Philippe Serp
    • 3
  • Anna M. Masdeu-Bultó
    • 2
    Email author
  • Montserrat Gómez
    • 1
    Email author
  1. 1.Laboratoire Hétérochimie Fondamentale et Appliquée, UMR CNRS 5069Université Paul SabatierToulouse cedex 9France
  2. 2.Departament de Química Física i InorgànicaUniversitat Rovira i VirgiliTarragonaSpain
  3. 3.Laboratoire de Chimie de Coordination, Composante ENSIACETToulouse cedex 4France

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