Elsevier

Tetrahedron Letters

Volume 46, Issue 16, 18 April 2005, Pages 2911-2914
Tetrahedron Letters

Regioselective synthesis of [1,2,3]-triazoles catalyzed by Cu(I) generated in situ from Cu(0) nanosize activated powder and amine hydrochloride salts

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Abstract

A straightforward and efficient method for the regioselective synthesis of functionalized 1,4-disubstituted [1,2,3]-triazoles, from terminal alkynes and azides, has been established utilizing Cu(0) as the source of the catalytic species. The presumed catalytic Cu(I) species is generated by the combination of 10 mol % copper nanosize activated powder and 1 equiv of an amine hydrochloride salt. The addition of an amine hydrochloride salt into the reaction mixture enhanced the dissolution of copper metal, and subsequently facilitated the formation of the Cu(I)-acetylide intermediate required for the regioselective cycloaddition.

References and notes (14)

  • R. HuisgenC.-K. Sha et al.S. Karlsson et al.

    Org. Prep. Proced. Int.

    (2001)
    K.V. Gothelf et al.

    Chem. Rev.

    (1998)
  • H. DehneH. WamhoffR. Böhm et al.

    Pharmazie

    (1981)
  • W. Winter et al.

    Chem. Ber.

    (1974)
    J. Bastide et al.
  • F. Palacios et al.

    Org. Prep. Proced. Int.

    (1995)
    D.J. Hlasta et al.

    J. Org. Chem.

    (1994)
    W.L. Mock et al.

    J. Org. Chem.

    (1989)
    W. Peng et al.

    Synlett

    (2003)
  • C.W. Tornoe et al.

    J. Org. Chem.

    (2002)
    V.V. Rostovtsev et al.

    Angew. Chem., Int. Ed.

    (2002)
    S. Kamijo et al.

    J. Am. Chem. Soc.

    (2003)
    P. Appukkuttan et al.

    Org. Lett.

    (2004)
  • Spectral data for compound 3a: 1H NMR (D2O) δ 7.96 (s, 1H), 7.27–7.20 (m, 5H), 5.46 (s, 2H), 4.64 (s, 2H); 13C NMR...
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