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Synthesis 2009(14): 2316-2318  
DOI: 10.1055/s-0029-1216815
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Symmetrical Ketones from Grignard Reagents and 1,1′-Carbonyldiimidazole

Daniela Bottalico, Vito Fiandanese, Giuseppe Marchese*, Angela Punzi
Dipartimento di Chimica, Università di Bari, Via Orabona 4, 70126 Bari, Italy
Fax: +39(80)5442075; e-Mail: marchese@chimica.uniba.it;
Further Information

Publication History

Received 19 February 2009
Publication Date:
14 May 2009 (online)

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Abstract

Coupling reactions of 1,1′-carbonyldiimidazole with Grignard reagents provide a rapid and straightforward method for the synthesis of symmetrical ketones.

Key words

Grignard reactions - coupling - acylations - 1,1′-carbonyldiimidazole - ketones

    References

  • 1a O’Neill BT. In Comprehensive Organic Synthesis   Vol. 1:  Trost BM. Fleming I. Schreiber SL. Pergamon; Oxford: 1991.  p.397 
    Google Scholar
  • 1b Larock RC. Comprehensive Organic Transformations   2nd ed.:  Wiley-VCH; New York: 1999. 
    Google Scholar
  • 1c Dieter RK. Tetrahedron  1999,  55:  4177 ; and references cited therein
    Google Scholar
  • 1d Smith BM. March J. Advanced Organic Chemistry   5th ed.:  Wiley; Chichester: 2001. 
    Google Scholar
  • 2a Shirley DA. Org. React.  1954,  8:  28 
    Google Scholar
  • 2b Jorgenson MJ. Org. React.  1970,  18:  1 
    Google Scholar
  • For some recent examples on the reactions of organometallic reagents with the most commonly used acyl chlorides or Weinreb amides, see:
  • 3a Dieter RK. Sharma RR. Yu H. Gore VK. Tetrahedron  2003,  59:  1083 
    Google Scholar
  • 3b Zhang Y. Rovis T. J. Am. Chem. Soc.  2004,  126:  15964 
    Google Scholar
  • 3c Taillier C. Bellosta V. Meyer C. Cossy J. Org. Lett.  2004,  6:  2145 
    Google Scholar
  • 3d Babudri F. Fiandanese V. Marchese G. Punzi A. J. Organomet. Chem.  2004,  689:  326 
    Google Scholar
  • 3e Oh CH. Reddy R. Tetrahedron Lett.  2004,  45:  8545 
    Google Scholar
  • 3f Wang X.-j. Zhang L. Sun X. Xu Y. Krishnamurty D. Senanayake CH. Org. Lett.  2005,  7:  5593 
    Google Scholar
  • 3g Conrad K. Hsiao Y. Miller R. Tetrahedron Lett.  2005,  46:  8587 
    Google Scholar
  • 3h Kangani CO. Kelley DE. Day BW. Tetrahedron Lett.  2006,  47:  6289 
    Google Scholar
  • 3i Crestey F. Stiebing S. Legay R. Collot V. Rault S. Tetrahedron  2007,  63:  419 
    Google Scholar
  • For some recent examples involving other carboxylic acid derivatives and organometallic reagents, see:
  • 4a Katritzky AR. Le KNB. Mohapatra PP. Synthesis  2007,  3141 
    Google Scholar
  • 4b Katritzky AR. Le KNB. Khelashvili L. Mohapatra PP. J. Org. Chem.  2006,  71:  9861 
    Google Scholar
  • 4c Werner T. Barrett GM. J. Org. Chem.  2006,  71:  4302 
    Google Scholar
  • 4d Wang D. Zhang Z. Org. Lett.  2003,  5:  4645 
    Google Scholar
  • 4e Wittenberg R. Srogl J. Egi M. Liebeskind LS. Org. Lett.  2003,  5:  3033 
    Google Scholar
  • 4f MaGee DI. Mallais TC. Eic M. Tetrahedron: Asymmetry  2003,  14:  3177 
    Google Scholar
  • 5 Bottalico D. Fiandanese V. Marchese G. Punzi A. Synlett  2007,  974 ; and references cited therein
    Article in Thieme ConnectGoogle Scholar
  • 6a Staab HA. Bauer H. Schneider KM. Azolides in Organic Synthesis and Biochemistry   Wiley-VCH; Weinheim: 1998. 
    Google Scholar
  • 6b Bonini BF. Comes-Franchini M. Fochi M. Mazzanti G. Ricci A. Varchi G. Synlett  1998,  1013 ; and references cited therein
    Google Scholar
  • 7 Ishiyama T. Hartwig J. J. Am. Chem. Soc.  2000,  122:  12043 
    CrossrefGoogle Scholar
  • 8 Kangani CO. Day BW. Org. Lett.  2008,  10:  2645 
    CrossrefGoogle Scholar
  • 9 Tartaglia S. Pace F. Scafato P. Rosini C. Org. Lett.  2008,  10:  3421 
    CrossrefGoogle Scholar
  • 12 Rao MLN. Periasamy M. Tetrahedron Lett.  1995,  36:  9069 
    CrossrefGoogle Scholar
10

Aldrich Catalogue, 2009-2010.

11

TCI Europe Catalogue, 2008-2009.