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Synlett 2009(2): 276-278  
DOI: 10.1055/s-0028-1087664
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

FeCl3-Catalyzed Reduction of Ketones and Aldehydes to Alkane Compounds

Christophe Dal Zotto, David Virieux, Jean-Marc Campagne*
Institut Charles Gerhardt Montpellier, ENSCM, 8 Rue de l’Ecole Normale, 34296 Montpellier, France
e-Mail: jean-marc.campagne@enscm.fr;
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Publication History

Received 18 September 2008
Publication Date:
15 January 2009 (online)

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Abstract

Ketones can efficiently be reduced to the corresponding methylene compound using the convenient and inexpensive combination of PMHS and FeCl3.

Key words

iron - reduction - ketones

    References

  • For recent reviews, see:
  • 1a Bolm C. Legros J. Le Paih J. Zani L. Chem. Rev.  2004,  104:  6217 
    Search in Google Scholar
  • 1b Enthaler S. Junge K. Beller M. Angew. Chem. Int. Ed.  2008,  47:  3317 
    Search in Google Scholar
  • 1c Correa A. García Mancheño O. Bolm C. Chem. Soc. Rev.  2008,  37:  1108 
    Search in Google Scholar
  • 2 Fürstner A. Majima K. Martin R. Krause H. Kattnig E. Goddard R. Lehmann CW. J. Am. Chem. Soc.  2008,  130:  1992 
    Search in Google Scholar
  • 3a Mimoun H. J. Org. Chem.  1999,  64:  2582 
    Search in Google Scholar
  • 3b Riant O. Mostefaï N. Courmacel J. Synthesis  2004,  2943 
  • 3c Gevorgyan V. Rubin M. Benson S. Liu J.-X. Yamamoto Y. J. Org. Chem.  2000,  65:  6179 
    Search in Google Scholar
  • 3d Mimoun H. De Saint Laumer J.-Y. Giannini L. Scopelliti R. Floriani C. J. Am. Chem. Soc.  1999,  121:  6158 
    Search in Google Scholar
  • 4a Brunner H. Fisch K. J. Organomet. Chem.  1991,  412:  11 
    Search in Google Scholar
  • 4b Furuta A. Nishiyama H. Tetrahedron Lett.  2008,  49:  110 
    Search in Google Scholar
  • 4c Furuta A. Nishiyama H. Chem. Commun.  2007,  760 
  • 4d Bart SC. Lobkovsky E. Chirik PJ. Org. Lett.  2008,  10:  2789 
    Search in Google Scholar
  • 4e Tondreau AM. Lobkovsky E. Chirik PJ. J. Am. Chem. Soc.  2004,  126:  13794 
    Search in Google Scholar
  • 4f Shaikh NS. Junge K. Beller M. Org. Lett.  2007,  9:  5429 
    Search in Google Scholar
  • 5a Shaikh NS. Enthaler S. Junge K. Beller M. Angew. Chem. Int. Ed.  2008,  47:  2497 
    Search in Google Scholar
  • 5b Langlotz BK. Wadepohl H. Gade LH. Angew. Chem. Int. Ed.  2008,  47:  4670 
    Search in Google Scholar
  • 6a Michaux J. Terrasson V. Marque S. Wehbe J. Prim D. Campagne JM. Eur. J. Org. Chem.  2007,  2601 
  • 6b Terrason V. Michaux J. Gaucher A. Wehbe J. Marque S. Prim D. Campagne JM. Eur. J. Org. Chem.  2007,  5332 
  • 6c Dal Zotto C. Wehbe J. Virieux D. Campagne JM. Synlett  2008,  2033 
  • 7 Kürti L. Czako B. Strategic Applications of Named Reactions in Organic Synthesis   Elsevier; Amsterdam: 2005.  p.92 
  • 8 Kürti L. Czako B. Strategic Applications of Named Reactions in Organic Synthesis   Elsevier; Amsterdam: 2005.  p.496 
  • 9 Chandrasekhar S. Raji Reddy C. Nagendra Babu B. J. Org. Chem.  2002,  67:  9080 
    CrossrefPubMedSearch in Google Scholar