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

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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.

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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.

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Authors and Affiliations

  1. Instituto de Tecnologia Química e Biológica da Universidade Nova de Lisboa, Av. da República, EAN, 2780-157, Oeiras, Portugal

    Rita Lopes, João M. S. Cardoso, Lorena Postigo & Beatriz Royo

Authors
  1. Rita Lopes
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  2. João M. S. Cardoso
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  3. Lorena Postigo
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  4. Beatriz Royo
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Correspondence to Beatriz Royo.

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Lopes, R., Cardoso, J.M.S., Postigo, L. et al. Reduction of Ketones with Silanes Catalysed by a Cyclopentadienyl-Functionalised N-Heterocyclic Iron Complex. Catal Lett 143, 1061–1066 (2013). https://doi.org/10.1007/s10562-013-1081-8

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  • DOI: https://doi.org/10.1007/s10562-013-1081-8

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