Synthesis 2006(15): 2585-2589  
DOI: 10.1055/s-2006-942469
PAPER
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Amination of Chloro-Terpyridine for the Preparation of Amine-Containing Ruthenium(II) Complexes

Olof Johansson*
Department of Photochemistry and Molecular Science, The Ångström Laboratories, Uppsala University, Box 523, 751 20 Uppsala, Sweden
Fax: +46(18)4716844; e-Mail: olof.johansson@fotomol.uu.se;
Further Information

Publication History

Received 3 February 2006
Publication Date:
04 July 2006 (eFirst)

Abstract

The palladium-catalyzed amination reaction of commercially available 4′-chloro-2,2′:6′,2′′-terpyridine opens an easy access to aminated mono- and ditopic terpyridine ligands. The obtained compounds were subsequently used to prepare new amine-containing ruthenium(II) polypyridyl complexes.

    References

  • 1 Baranoff E. Collin J.-P. Flamigni L. Sauvage J.-P. Chem. Soc. Rev.  2004,  33:  147 
  • 2 Andres PR. Schubert US. Adv. Mater.  2004,  16:  1043 
  • 3 Constable EC. Handel RW. Housecroft CE. Farrán Morales A. Ventura B. Flamigni L. Barigelletti F. Chem. Eur. J.  2005,  11:  4024 
  • 4 Medlycott EA. Hanan GS. Chem. Soc. Rev.  2005,  34:  133 ; and references cited therein
  • 5a Martineau D. Beley M. Gros P. J. Org. Chem.  2006,  71:  566 
  • 5b Wang J. Fang Y.-Q. Hanan GS. Loiseau F. Campagna S. Inorg. Chem.  2005,  44:  5 
  • 5c Martineau D. Gros P. Beley M. Fort Y. Eur. J. Inorg. Chem.  2004,  3984 
  • 6 Johansson O. Lomoth R. Chem. Commun.  2005,  1578 
  • 7 Wolfe JP. Wagaw S. Marcoux J.-F. Buchwald SL. Acc. Chem. Res.  1998,  31:  805 
  • 8a Shen Q. Shekhar S. Stambuli JP. Hartwig JF. Angew. Chem. Int. Ed.  2005,  44:  1371 
  • 8b Ji J. Li T. Bunnelle WH. Org. Lett.  2003,  5:  4611 
  • 8c Wolfe JP. Tomori H. Sadighi JP. Yin J. Buchwald SL. J. Org. Chem.  2000,  65:  1158 
  • 9a Charles MD. Schultz P. Buchwald SL. Org. Lett.  2005,  7:  3965 
  • 9b Hooper MW. Hartwig JF. Organometallics  2003,  22:  3394 
  • 9c Hooper MW. Utsunomiya M. Hartwig JF. J. Org. Chem.  2003,  68:  2861 
  • 9d Ogawa K. Radke KR. Rothstein SD. Rasmussen SC. J. Org. Chem.  2001,  66:  9067 
  • 10a Ruloff R. van Koten G. Merbach AE. Chem. Commun.  2004,  842 
  • 10b Fallahpour R.-A. Synthesis  2003,  155 
  • 10c Whittle B. Batten SR. Jeffery JC. Rees LH. Ward MD. J. Chem. Soc., Dalton Trans.  1996,  4249 
  • 11a Wieprecht T, Schlingloff G, Xia J, Heinz U, Schneider A, Dubs M.-J, Bachmann F, Hazenkamp M, and Dannache J. inventors; PCT Int. Appl.  WO2004/039933 A1.  2004; Chem. Abstr. 2004, 140, 408683
  • 11b Wieprecht T. Xia J. Heinz U. Dannacher J. Schlingloff G. J. Mol. Catal. A: Chem.  2003,  203:  113 
  • 11c Constable EC. Cargill Thompson AMW. Tocher DA. Daniels MAM. New J. Chem.  1992,  16:  855 
  • 12a Fallahpour R.-A. Neuburger M. Zehnder M. New J. Chem.  1999,  53 
  • 12b Fallahpour R.-A. Eur. J. Inorg. Chem.  1998,  1205 
  • 13 Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4685 
  • 14 Ziessel R. Grosshenny V. Hissler M. Stroh C. Inorg. Chem.  2004,  43:  4262 
  • 15 Abrahamsson M. Wolpher H. Johansson O. Larsson J. Kritikos M. Eriksson L. Norrby P.-O. Bergquist J. Sun L. Åkermark B. Hammarström L. Inorg. Chem.  2005,  44:  3215 
  • 16 Ward MD. Chem. Soc. Rev.  1995,  24:  121 
  • 17 Evans IP. Spencer A. Wilkinson G. J. Chem. Soc., Dalton Trans.  1973,  204 
  • 18 Johansson O. Borgström M. Lomoth R. Palmblad M. Bergquist J. Hammarström L. Sun L. Åkermark B. Inorg. Chem.  2003,  42:  2908