Synthesis 2011(9): 1361-1364  
DOI: 10.1055/s-0030-1259986
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Unsymmetrical, Monosubstituted Bis-terpyridine Derivatives via Suzuki-Miyaura Cross-Coupling

Jinghua Lia, Takashi Satob, Hongfang Lib, Masayoshi Higuchi*a,b,c
a Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba 305-8577, Japan
b International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan
Fax: +81(29)8604721; e-Mail: higuchi.masayoshi@nims.go.jp;
c JST-CREST, Japan Science and Technology Agency, Saitama 332-0012, Japan
Further Information

Publication History

Received 26 January 2011
Publication Date:
04 April 2011 (online)

Abstract

As building blocks for metallo-supramolecular polymers, novel, unsymmetrical, monosubstituted bis-terpyridine derivatives with one electron-donating (OMe) or electron-withdrawing (CN or COOMe) group have been synthesized via the Suzuki-Miyaura cross-coupling reaction. This method is quick, efficient and suitable for the introduction of various substituents at the periphery of pyridine.

    References

  • 1a Schubert US. Eschbaumer C. Angew. Chem. Int. Ed.  2002,  41:  2892 
  • 1b Higuchi MC. Akasaka Y. Ikeda T. Hayashi A. Kurth DG. J. Inorg. Organomet. Polym. Mater.  2009,  19:  74 
  • 2a Andres PR. Schubert US. Adv. Mater. (Weinheim, Ger.)  2004,  16:  1043 
  • 2b Carlson CN. Kuehl CJ. Da-Re RE. Veauthier JM. Schelter EJ. Milligan AE. Scott BL. Bauer ED. Thompson JD. Morris DE. John KD. J. Am. Chem. Soc.  2006,  128:  7230 
  • 3a Mortimer RJ. Dyer AL. Reynolds JR. Displays  2006,  27:  2 
  • 3b Daniher AT. Bashkin JK. Chem. Commun.  1998,  1077 
  • 3c Carter PJ. Cheng C.-C. Thorp HH. J. Am. Chem. Soc.  1998,  120:  632 
  • 4a Han FS. Higuchi M. Kurth DG. Org. Lett.  2007,  9:  559 
  • 4b Li J.-H. Higuchi M. J. Inorg. Organomet. Polym. Mater.  2010,  20:  10 
  • 5 Eryazici I. Moorefield CN. Durmus S. Newkome GR. J. Org. Chem.  2006,  71:  1009 
  • 6a Thummel RP. Jahng Y. J. Org. Chem.  1985,  50:  3635 
  • 6b Nishioka T. Yuan J. Yamamoto Y. Sumitomo K. Wang Z. Hashino K. Hosoya C. Ikawa K. Wang G. Matsumoto K. Inorg. Chem.  2006,  45:  4088 
  • 7 Choi JS. Kang CW. Jung K. Yang JW. Kim YG. Han H. J. Am. Chem. Soc.  2004,  126:  8606 
  • 8 Ishiyama T. Itoh Y. Kitano T. Miyaura N. Tetrahedron Lett.  1997,  38:  3447