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

Fahmi Himo, Timothy Lovell, Robert Hilgraf, Vsevolod V. Rostovtsev, Louis Noodleman, K. Barry Sharpless, Valery V. Fokin

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1188 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)210-216
Number of pages7
JournalJournal of the American Chemical Society
Volume127
Issue number1
DOIs
Publication statusPublished - 12 Jan 2005
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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    Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V. V., Noodleman, L., Sharpless, K. B., & Fokin, V. V. (2005). Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. Journal of the American Chemical Society, 127(1), 210-216. https://doi.org/10.1021/ja0471525