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Synlett 2003(12): 1874-1876  
DOI: 10.1055/s-2003-41472
LETTER
© Georg Thieme Verlag Stuttgart · New York

Direct Synthesis of Benzoylpyridines from Chloropyridines via a Palladium-Carbene Catalyzed Carbonylative Suzuki Cross-Coupling Reaction

Eddy Maertena, Fatima Hassounaa, Samuel Couve-Bonnairea, André Mortreuxa, Jean-François Carpentierb, Yves Castanet*a
a Laboratoire de Catalyse de Lille, UMR 8010 CNRS, Université de Lille 1, ENSCL, BP 108, 59652, Villeneuve d’Ascq Cedex, France
Fax: +33(3)20436585; e-Mail: yves.castanet@ensc-lille.fr;
b Organométalliques et Catalyse, UMR 6509 CNRS, Université de Rennes 1, Institut de Chimie, Campus de Beaulieu, 35042, Rennes Cedex, France
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Publikationsverlauf

Received 17 June 2003
Publikationsdatum:
19. September 2003 (online)

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Abstract

The use of N-heterocyclic carbene-type ligands with palladium catalysts allows the activation of chloropyridines and chloroquinoline towards carbonylative cross-coupling with phenylboronic acid for the synthesis of unsymmetrical biaryl ketones.

Key words

palladium - N-heterocyclic carbene ligand - pyridyl chloride

    References

  • For reviews, see:
  • 1a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • 1b Suzuki A. In Handbook of Organopalladium Chemistry for Organic Synthesis   Vol 1:  Negishi EI. John Wiley and Sons, Inc.; Hoboken: 2002.  p.249-262  
    Google Scholar
  • 2 For a recent review, see: Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Google Scholar
  • 3a Ishiyama T. Kizaki H. Miyaura N. Suzuki A. Tetrahedron Lett.  1993,  34:  7595 
    CrossrefGoogle Scholar
  • 3b Ishiyama T. Kizaki H. Hayashi T. Suzuki A. Miyaura N. J. Org. Chem.  1998,  63:  4726 
    CrossrefGoogle Scholar
  • 4a Couve-Bonnaire S. Carpentier J.-F. Mortreux A. Castanet Y. Tetrahedron Lett.  2001,  42:  3689 
    CrossrefGoogle Scholar
  • 4b Couve-Bonnaire S. Carpentier J.-F. Mortreux A. Castanet Y. Tetrahedron  2003,  59:  2793 
    CrossrefGoogle Scholar
  • 5a Zhang C. Huang J. Trudell MT. Nolan SP. J. Org. Chem.  1999,  64:  3804 
    CrossrefPubMedGoogle Scholar
  • 5b Grasa GA. Viciu MS. Huang J. Zhang C. Trudell ML. Nolan SP. Organometallics  2002,  21:  2866 
    CrossrefPubMedGoogle Scholar
  • 5c McGuiness D. Cavell KJ. Organometallics  2000,  19:  741 
    CrossrefPubMedGoogle Scholar
  • 5d Gstöttmayr CWK. Böhn VPM. Herdtweck E. Grosche M. Herrmann WA. Angew. Chem. Int. Ed.  2002,  41:  1363 
    CrossrefPubMedGoogle Scholar
  • 6 As our investigations neared completion, palladium-imidazolium carbonylative coupling of more actived aryl diazonium ions with aryl boronic acids was reported: Andrus MB. Ma Y. Zang Y. Song C. Tetrahedron Lett.  2002,  43:  9137 
    Google Scholar
  • 7a Littke AD. Dai C. Fu GC. J. Am. Chem. Soc.  2000,  122:  4020 
    CrossrefPubMedGoogle Scholar
  • 7b Yin J. Rainka MP. Zhang X.-X. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  1162 
    CrossrefPubMedGoogle Scholar
  • 8 Arduengo AJ. Krafczyk R. Schmutzler R. Craig HA. Goerlich JR. Marshall WJ. Unverzagt M. Tetrahedron  1999,  55:  14523 
    Google Scholar
9

In a number of coupling reactions of aryl chlorides, it was found that a 1:1 Pd-ligand ratio (ligand = N-heterocyclic carbene, phosphine, …) led to optimum reaction rates (see ref. 2 and ref. 5b for N-heterocyclic carbene ligands).

10

TOF: turnover frequencies defined as the number of moles of substrate transformed per mole of catalyst and per hour calculated after one hour of reaction.