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;
Further Information

Publication History

Received 11 February 2005
Publication Date:
21 April 2005 (online)

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.

    References

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