Download PDF
Synthesis 2004(1): 23-25  
DOI: 10.1055/s-2003-42490
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cyanation Reactions of Thiophene Halides

Thomas Erker*, Stephanie Nemec
Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria
Fax: +43(1)42779551; e-Mail: thomas.erker@univie.ac.at;
Further Information

Publication History

Received 20 October 2003
Publication Date:
17 November 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

The described method provides an efficient cyanation reaction of thiophene halides using tris(dibenzylidene-acetone)di­palladium(0), 1,1′-bis-(diphenylphosphino)ferrocene) and zinc powder as the catalyst system and Zn(CN)2 as the cyanide source. Several thiophenes with various substituents are effectively cyanated under these conditions.

Key words

nitriles - thiophene - palladium - catalysis - cyanation

    References

  • 1 Studies on the Chemistry of Thioannelated O,N- and S,N- containing heterocycles - Part 32. For Part 31, see: Erker T. Trinkl K. Scientia Pharmaceutica  2003,  71:  51 
    Google Scholar
  • 2a Mowry DT. Chem. Rev.  1948,  42:  189 
    CrossrefGoogle Scholar
  • 2b Grashey R. Comp. Org. Chem.  1991,  6:  225 
    CrossrefGoogle Scholar
  • 2c Okano T. Kiji J. Toyooka Y. Chem. Lett.  1998,  426 
    CrossrefGoogle Scholar
  • 2d Anderson BA. Bell EC. Ginah FO. Harn NK. Pagh LM. Wepsiec JP. J. Org. Chem.  1998,  63:  8224 
    CrossrefGoogle Scholar
  • 2e Tschaen DM. Desmond R. King AO. Fortin MC. Pipik B. King S. Verhoeven TR. Synth. Commun.  1994,  24:  887 
    CrossrefGoogle Scholar
  • 3a Heck RF. Palladium Reagents in Organic Synthesis   Academic; New York: 1985. 
    CrossrefGoogle Scholar
  • 3b Chatani N. Hanafusa T. J. Org. Chem.  1986,  51:  4714 
    CrossrefGoogle Scholar
  • 3c Sakamoto T. Oshawa K. J. Chem. Soc., Perkin Trans. 1  1999,  2323 
    CrossrefGoogle Scholar
  • 4 Jin F. Confalone PN. Tetrahedron Lett.  2000,  41:  3271 
    CrossrefGoogle Scholar
  • 5a Selnick AG. Smith GR. Tebben AJ. Synth. Commun.  1995,  25:  3255 
    Google Scholar
  • 5b Kubota H. Rice KC. Tetrahedron Lett.  1998,  39:  2970 
    Google Scholar
  • 6 Helbert M. Berthelot M. Laurence C. Spinelli D. Consiglio G. Amone C. Spectrochim. Acta, Part A  1983,  39:  703 
    CrossrefGoogle Scholar
  • 7 Arakawa S. Veda N. Shigemasa Y. Nakashima R. Tottori Daigaku Nogakubu Kenkyu Hokoku  1982,  13:  69 
    Google Scholar
  • 8 Lohaus G. Chem. Ber.  1967,  100(8):  2719 
    CrossrefGoogle Scholar
  • 9 Morel J. Paulmier C. Pastour P. C. R. Acad. Sci., Paris, Ser. C  1968,  266:  1300 
    Google Scholar
  • 10 Seth-Paul WA. Van der Veken BJ. Can. J. Spectrosc.  1978,  23:  74 
    Google Scholar
  • 11 Dubus P. Decroix B. Morel J. Paulmier C. C. R. Acad. Sci., Ser. C  1974,  278(1):  61 
    Google Scholar
  • 12 Baltrop JA. Day AC. Irving E. J. Chem. Soc., Chem. Commun.  1979,  20:  881 
    Google Scholar
  • 13 Fournari P. Guiland R. Person M. Bull. Soc. Chim. Fr.  1967,  11:  4115 
    Google Scholar
  • 14 Holland GF. inventors; U. S. Patent  4282246. 
  • 15 Suzuki H. Iwaro T. Sugiyama T. Bull. Inst. Chem. Res., Kyoto Univ.  1974,  52:  561 
    Google Scholar