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

By F. Himo, T. Lovell, Robert Hilgraf, V. Rostovtsev, Louis Noodleman, K. Sharpless, Valery Fokin. Journal of the American Chemical Society, 2004

1,497 citations recorded by the source corpus.

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.

Subfields: Organic Chemistry

View Paper: https://www.semanticscholar.org/paper/33e904b9d4ce03fbc56a8cc58aab0e50d27173cc