PDF icon Download PDF
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;
Further Information

Publication History

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

   Permissions and Reprints All articles of this category
Preview

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