Download PDF
Synthesis 2009(19): 3214-3218  
DOI: 10.1055/s-0029-1216958
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Stille Cross-Coupling Reactions of 2-(Tributylstannyl)- and 2,5-Bis(trimethylstannyl)tellurophene

Daniel P. Sweat, Chad E. Stephens*
Department of Chemistry and Physics, Augusta State University, Augusta, GA 30904, USA
Fax: +1(706)4345597; e-Mail: cstephe7@aug.edu;
Further Information

Publication History

Received 30 March 2009
Publication Date:
21 August 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Herein, we describe the synthesis and Stille cross-coupling reactions of 2-(tributylstannyl)- and 2,5-bis(trimethylstannyl)tellurophene. The reactions were most optimal when using aryl iodides as coupling partners, and a mixed catalyst system consisting of tetrakis(triphenylphosphine)palladium(0) and copper(I) iodide, together with cesium fluoride as additive, in N,N-dimethylform­amide. This is the first reported synthesis and use of stannylated tellurophenes for cross-coupling reactions.

Key words

tellurophene - Stille reaction - cross-coupling - palladium - heterocyclic

    References

  • 1a Corbet J.-P. Mignani G. Chem. Rev.  2006,  106:  2651 
    Google Scholar
  • 1b Li JJ. Gribble GW. Palladium in Heterocyclic Chemistry   2nd ed:  Elsevier Ltd.; Amsterdam: 2007. 
    Google Scholar
  • 2a Cross-Coupling Reactions: A Practical Guide   Miyaura N. Springer-Verlag; Berlin / Heidelberg: 2002. 
    Google Scholar
  • 2b Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4442 
    Google Scholar
  • 3 Farina V. Krishnamurthy V. Scott WJ. Organic Reactions   Vol. 50:  Paquette L. Wiley; New York: 1997. 
    Google Scholar
  • 4 Liu Y. Collar CJ. Kumar A. Stephens CE. Boykin DW. Wilson WD. J. Phys. Chem. B  2008,  112:  11809 
    CrossrefGoogle Scholar
  • 5a Rosypal AC. Werbovetz KA. Salem M. Stephens CE. Kumar A. Boykin DW. Hall JE. Tidwell RR. J. Parasitol.  2008,  94:  743 
    Google Scholar
  • 5b Silva CF. Batista MM. Mota RA. de Souza EM. Stephens CE. Som P. Boykin DW. Soeiro MNC. Biochem. Pharmacol.  2007,  73:  1939 
    Google Scholar
  • 6a Inoue S. Jigami T. Nozoe H. Otsubo T. Ogura F. Tetrahedron Lett.  1994,  35:  8009 
    Google Scholar
  • 6b Inoue S. Jigami T. Nozoe H. Aso Y. Ogura F. Otsubo T. Heterocycles  2000,  52:  159 
    Google Scholar
  • 7 Stephens CE. Tanious F. Kim S. Wilson WD. Schell WA. Perfect JR. Franzblau SG. Boykin DW. J. Med. Chem.  2001,  44:  1741 
    Google Scholar
  • 8 Gronowitz S. Peters D. Heterocycles  1990,  30:  645 
    CrossrefGoogle Scholar
  • 9a Zeni G. Tetrahedron Lett.  2005,  46:  2647 
    Google Scholar
  • 9b Panatieri RB. Reis JS. Borges LP. Nogueira CW. Zeni G. Synlett  2006,  3161 
    Google Scholar
  • 10 The synthesis and coupling reaction of a related benzo[b]tellurophene-3-boronic acid derivative has been described, see: Jones RL. Dissertation   Technische Universität Kaiserslautern; Germany: 2005. 
    Google Scholar
  • 11 Seitz DE. Lee S.-H. Hanson RN. Bottaro JC. Synth. Commun.  1983,  13:  121 
    CrossrefGoogle Scholar
  • 12 Gonzalez JL. Stephens CE. Wenzler T. Brun R. Tanious FA. Wilson WD. Barszcz T. Werbovetz KA. Boykin DW. Eur. J. Med. Chem.  2007,  42:  552 
    CrossrefGoogle Scholar
  • 13 Tierney S. Heeney M. McCulloch L. Synth. Met.  2005,  148:  195 
    CrossrefGoogle Scholar
  • 14a Mee SPH. Lee V. Baldwin JE. Chem. Eur. J.  2005,  11:  3294 
    Google Scholar
  • 14b Mee SPH. Lee V. Baldwin JE. Angew. Chem. Int. Ed.  2004,  43:  1132 
    Google Scholar
  • 15 Sweat DP. Stephens CE. J. Organomet. Chem.  2008,  693:  2463 
    CrossrefGoogle Scholar
  • 16 Fringuelli F. Serena B. Taticchi A. J. Chem. Soc., Perkin Trans. 2  1980,  971 
    CrossrefGoogle Scholar
  • 17 Dabdoub MJ. Dabdoub VB. Pereira MA. Zukerman-Schpector J. J. Org. Chem.  1996,  61:  9503 
    CrossrefGoogle Scholar