Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates
Fahmi Himo(Scripps Research Institute), Timothy Lovell(Scripps Research Institute), Robert Hilgraf(Scripps Research Institute), Vsevolod V. Rostovtsev(Scripps Research Institute), Louis Noodleman(Scripps Research Institute), K. Barry Sharpless(Scripps Research Institute), Valery V. Fokin(Scripps Research Institute)
Cited by 1,671
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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