Download PDF
Synlett 2006(18): 3161-3163  
DOI: 10.1055/s-2006-941593
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-Alkynyl-Tellurophene Derivatives via Palladium-Catalyzed Cross-Coupling

Rodrigo B. Panatieri, Joel S. Reis, Lysandro P. Borges, Cristina W. Nogueira, Gilson Zeni*
Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul, CEP 97105-900, Brazil
Fax: +55(55)32208978; e-Mail: gzeni@quimica.ufsm.br;
Further Information

Publication History

Received 24 January 2006
Publication Date:
29 June 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

We present herein our results on the palladium-catalyzed cross-coupling of 2-halotellurophene with several terminal alkynes to give the 2-alkynyl-tellurophene derivatives in excellent yields. The reaction proceeded cleanly under mild conditions and was performed with propargyl alcohols, propargyl amines, propiolate, as well as alkyl and aryl alkynes, in the presence of PdCl2(PPh3)2, Et3N, THF and CuI.

Key words

vinylic tellurides - palladium - cross-coupling - telluro­phene - Sonogashira

    References and Notes

  • 1a Zeni G. Braga AL. Stefani HA. Acc. Chem. Res.  2003,  36:  731 
    CrossrefGoogle Scholar
  • 1b Silveira CC. Braga AL. Vieira AS. Zeni G. J. Org. Chem.  2003,  68:  662 
    CrossrefGoogle Scholar
  • 1c Zeni G. Panatieri RB. Lissner E. Menezes PH. Braga AL. Stefani HA. Org. Lett.  2001,  3:  819 
    CrossrefGoogle Scholar
  • 2a Petragnani N. Stefani HA. Tetrahedron  2005,  61:  1613 
    CrossrefGoogle Scholar
  • 2b Organoselenium Chemistry, In Topics in Current Chemistry   Vol. 208:  Wirth T. Springer-Verlag; Heidelberg: 2000. 
    CrossrefGoogle Scholar
  • 2c Krief A. In Comprehensive Organometallic Chemistry II   Vol. 11:  Abel EV. Stone FGA. Wilkinson G. Pergamon Press; New York: 1995.  Chap. 13.
    CrossrefGoogle Scholar
  • 2d Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis, In Organic Chemistry Series 4   Baldwin JE. Pergamon Press; Oxford: 1986. 
    CrossrefGoogle Scholar
  • 2e Petragnani N. Tellurium in Organic Synthesis   Academic Press; London: 1994. 
    CrossrefGoogle Scholar
  • 3 Nogueira CW. Zeni G. Rocha JBT. Chem. Rev.  2004,  104:  6255 
    CrossrefGoogle Scholar
  • 4 Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett.  1975,  16:  4467 
    CrossrefGoogle Scholar
  • 5a Masui K. Ikegami H. Mori A. J. Am. Chem. Soc.  2004,  126:  5074 
    CrossrefGoogle Scholar
  • 5b Zeni G. Nogueira CW. Panatieri RB. Silva DO. Menezes PH. Braga AL. Silveira CC. Stefani HA. Rocha JBT. Tetrahedron Lett.  2001,  42:  7921 
    CrossrefGoogle Scholar
  • 5c Zeni G. Lüdtke DS. Nogueira CW. Panatieri RB. Braga AL. Silveira CC. Stefani HA. Rocha JBT. Tetrahedron Lett.  2001,  42:  8927 
    CrossrefGoogle Scholar
  • 5d Parrish JP. Jung YC. Floyd RJ. Jung KW. Tetrahedron Lett.  2002,  43:  7899 
    CrossrefGoogle Scholar
  • 6 The tellurophene derivatives were prepared according to: Barton TJ. Roth RW. J. Organomet. Chem.  1972,  39:  C66 
    CrossrefGoogle Scholar
  • 7 Inoue S. Jigami T. Nozoe H. Aso Y. Ogura F. Otsubo T. Heterocycles  2000,  52:  159 
    CrossrefGoogle Scholar
8

Typical Procedure for Cross-Coupling Reaction.
A 25-mL, two-necked, round-bottom flask equipped with a magnetic stir bar and argon was charged sequentially with Pd(PPh3)2Cl2 (10 mol%), CuI (10 mol%), THF (2.5 mL), 2-iodotellurophene (0.25 mmol), alkyne (0.75 mmol) and Et3N (0.5 mL). The mixture was stirred at r.t. for 12 h. After this time, the mixture was filtered through a pad of alumina eluting with 50 mL of EtOAc. The organic phase was concentrated under vacuum and the residue was purified by flash chromatography. Selected Spectral Data for 1-(5-Butyltellurophen-2-yl)pent-1-yn-3-ol.
1H NMR (400 MHz, CDCl3): δ = 7.54 (d, 1 H, J = 4.08 Hz), 7.17 (d, 1 H, J = 4.06 Hz), 4.5 (t, 1 H, 6.3 Hz), 2.84 (t, 2 H, 7.4 Hz), 2.30-2.15 (m, 1 H), 1.79 (quint, 2 H, J = 7.08 Hz), 1.60 (quint, 2 H, J = 7.8 Hz), 1.40 (sext, 2 H, J = 7.05), 1.03 (t, 3 H, J = 7.4 Hz), 0.92 (t, 3 H, J = 7.17 Hz). 13C NMR (100 MHz, CDCl3): δ = 156.63, 142.05, 133.60, 118.87, 95.97, 85.07, 64.47, 36.66, 36.37, 22.03, 13.74, 9.46.