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. 2005 Jan 12;127(1):210-6.
doi: 10.1021/ja0471525.

Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates

Fahmi Himo  1 , Timothy Lovell, Robert Hilgraf, Vsevolod V Rostovtsev, Louis Noodleman, K Barry Sharpless, Valery V Fokin
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Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates

Fahmi Himo et al. J Am Chem Soc. .

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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