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  • Title: Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.
    Author: Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV.
    Journal: J Am Chem Soc; 2005 Jan 12; 127(1):210-6. PubMed ID: 15631470.
    Abstract:
    Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles.
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