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Synlett 2005(8): 1251-1254  
DOI: 10.1055/s-2005-868481
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Facile Route to Sterically Hindered and Non-Hindered 4′-Aryl-2,2′:6′,2′′-Terpyridines

Jianhua Wang, Garry S. Hanan*
Département de Chimie, Université de Montréal, Montreal, Québec H3T 1J4, Canada
Fax: +1(514)3437586; e-Mail: garry.hanan@umontreal.ca;
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Publikationsverlauf

Received 11 February 2005
Publikationsdatum:
21. April 2005 (online)

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Abstract

A facile one-pot synthesis of 4′-aryl-2,2′:6′,2′′-terpyridines from aryl aldehydes and 2-acetylpyridine is presented. The synthesis of terpyridines incorporating sterically hindered aryl groups, such as the 9-anthryl group, can also be readily synthesized using this method.

Key words

nitrogen ligands - heterocycles - substituted terpyridines - one-pot reactions

    References

  • 1a Demas JM. DeGra BA. Coord. Chem. Rev.  2001,  211:  317 
    Google Scholar
  • 1b For a recent example: Kimura M. Takahashi A. Sakata T. Tsukahara K. Bull. Chem. Soc. Jpn.  1998,  71:  1839 
    Google Scholar
  • 1c Péchy P. Rotzinger FP. Nazeeruddin MK. Kohle O. Zakeeruddin SM. Humphry-Baker R. Grätzel M. J. Chem. Soc., Chem. Commun.  1995,  65 
    Google Scholar
  • 1d Baldo MA. Thompson ME. Forrest SR. Nature  2000,  403:  750 
    Google Scholar
  • 1e Ziessel RJ. Inclusion Phenom. Macrocyclic Chem.  1999,  35:  369 
    Google Scholar
  • 2 Constable EC. Cargill Thompson AMW. Tocher DA. Daniels MAM. New J. Chem.  1992,  16:  855 
    Google Scholar
  • 3 Sauvage J.-P. Collin J.-P. Chambron J.-C. Guillerez S. Coudret C. Balzani V. Barigelletti F. De Cola L. Flamigni L. Chem. Rev.  1994,  94:  993 
    CrossrefGoogle Scholar
  • 4a Maestri M. Armaroli N. Balzani V. Constable EC. Cargill Thompson AMW. Inorg. Chem.  1995,  34:  2759 
    CrossrefGoogle Scholar
  • 4b Hammarström L. Barigelletti F. Flamigni L. Indelli MT. Armaroli N. Calogero G. Guardigli M. Sour A. Collin J.-P. Sauvage J.-P. J. Phys. Chem. A  1997,  101:  9061 
    CrossrefGoogle Scholar
  • 4c Albano G. Balzani V. Constable EC. Maestri M. Smith DR. Inorg. Chim. Acta  1998,  277:  225 
    CrossrefGoogle Scholar
  • 5 Mutai T. Cheon J.-D. Arita S. Araki K. J. Chem. Soc., Perkin Trans. 2  2001,  1045 
    CrossrefGoogle Scholar
  • 6 Goodall W. Williams JAG. Chem. Commun.  2001,  2514 
    CrossrefGoogle Scholar
  • 7 Roberto D. Tessore F. Ugo R. Bruni S. Manfredi A. Quici S. Chem. Commun.  2002,  846 
    CrossrefGoogle Scholar
  • 8 Alcock NW. Barker PR. Haider JM. Hannon MJ. Painting CL. Pikramenou Z. Plummer EA. Rissanen K. Saarenketo P. J. Chem. Soc., Dalton Trans.  2000,  1447 
    CrossrefGoogle Scholar
  • 9 A comprehensive review of methods up to 1995 is provided by: Cargill Thompson AMW. Coord. Chem. Rev.  1997,  160:  1 
    CrossrefGoogle Scholar
  • 10a Kröhnke F. Synthesis  1976,  1 
    CrossrefGoogle Scholar
  • 10b Constable EC. Ward MD. Corr S. Inorg. Chim. Acta  1988,  141:  201 
    CrossrefGoogle Scholar
  • 10c Frank RL. Riener EF. J. Am. Chem. Soc.  1950,  72:  4182 
    CrossrefGoogle Scholar
  • 10d Korall P. Börje A. Norrby P.-O. Åkermark B. Acta Chem. Scand.  1997,  51:  760 
    CrossrefGoogle Scholar
  • 10e Cave GWV. Raston CL. Chem. Commun.  2000,  2199 
    CrossrefGoogle Scholar
  • 11a Cardenas DJ. Sauvage J.-P. Synlett  1996,  916 
    Google Scholar
  • 11b Hanan GS. Schubert US. Volkmer D. Riviere E. Lehn J.-M. Kyritsakas N. Fisher J. Can. J. Chem.  1997,  75:  169 
    Google Scholar
  • 11c Fallahpour R.-A. Neuberger M. Zehnder M. New J. Chem.  1999,  23:  53 
    Google Scholar
  • 11d Fallahpour R.-A. Eur. J. Inorg. Chem.  1998,  1205 
    Google Scholar
  • 12 Goodall W. Wild K. Arm KJ. Williams JAG. J. Chem. Soc., Perkin Trans. 2  2002,  1669 
    CrossrefGoogle Scholar
  • 13 During the preparation of this paper, a similar approach to synthesize 4′-p-tolyl-2,2′:6′,2′′-terpyridine was reported: Vaduvescu S. Potvin PG. Eur. J. Inorg. Chem.  2004,  1763 
    CrossrefGoogle Scholar
  • 14 Collin J.-P. Guillerez S. Sauvage J.-P. Barigelletti F. De Cola L. Flamigni L. Balzani V. Inorg. Chem.  1991,  30:  4230 
    CrossrefGoogle Scholar
  • 16 Wang J. Hanan GS. Loiseau F. Campagna S. Chem. Commun.  2004,  2068 
    CrossrefGoogle Scholar
  • 17 Yoo D.-W. Yoo S.-K. Kim C. Lee J.-K. J. Chem. Soc., Dalton Trans.  2002,  3931 
    CrossrefGoogle Scholar
  • 18 Michalec JF. Bejune SA. Cuttell DG. Summerton GC. Gertenbach JA. Field JS. Haines RJ. McMillin DR. Inorg. Chem.  2001,  40:  2193 
    CrossrefGoogle Scholar
  • 19 Husson J. Beley M. Kirsch G. Tetrahedron Lett.  2003,  44:  1767 
    CrossrefGoogle Scholar
  • 20 Persaud L. Barbiero G. Can. J. Chem.  1991,  69:  315 
    Google Scholar
15

Most of the starting aryl aldehydes were purchased from Aldrich. Aldehydes that were not commercial available were synthesized from the corresponding aryl bromides by lithiation and then formylation with dimethylformamide.