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Catalysis Letters

, Volume 143, Issue 10, pp 1061–1066 | Cite as

Reduction of Ketones with Silanes Catalysed by a Cyclopentadienyl-Functionalised N-Heterocyclic Iron Complex

  • Rita Lopes
  • João M. S. Cardoso
  • Lorena Postigo
  • Beatriz Royo
Article

Abstract

The well-defined piano-stool iron(II) complex (Cp-NHC)Fe(CO)I bearing a bidentate cyclopentadienyl-functionalised N-heterocyclic carbene ligand is shown to catalyse the reduction of ketones under mild conditions (1–2 h at room temperature) when combined with catalytic amounts of potassium tert-butoxide, and using Ph2SiH2 and the inexpensive and less reactive polymethylhydrosiloxane as reducing agents. The stoichiometric reaction of (Cp-NHC)Fe(CO)I with potassium tert-butoxide generates an iron-hydroxo complex, which seems to be the active species in the reduction of ketones.

Graphical Abstract

Keywords

N-heterocyclic carbenes Cyclopentadienyl Iron Reduction ketones Polymethylhydrosiloxane 

Notes

Acknowledgments

This study was supported by Fundação para a Ciência e a Tecnologia through projects PTDC/QUI–QUI/110349/2009 and PTDC/QUI–QUI/099389/2008. JMS Cardoso thanks FCT for the PhD fellowship SFRH/BD/66386/2009. The NMR spectrometers are part of the National NMR Network and REDE/1517/RMN/2005 supported with funds from POCI 2010 and FCT.

Supplementary material

10562_2013_1081_MOESM1_ESM.docx (518 kb)
Supplementary material (DOCX 518 kb)

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Rita Lopes
    • 1
  • João M. S. Cardoso
    • 1
  • Lorena Postigo
    • 1
  • Beatriz Royo
    • 1
  1. 1.Instituto de Tecnologia Química e Biológica da Universidade Nova de LisboaOeirasPortugal

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