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

Research output: Contribution to journalArticle

1127 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

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Isoxazoles
Azoles
Nitriles
Triazoles
Azides
Cycloaddition
Cycloaddition Reaction
Discrete Fourier transforms
Oxides
Copper

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

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

In: Journal of the American Chemical Society, Vol. 127, No. 1, 12.01.2005, p. 210-216.

Research output: Contribution to journalArticle

Himo, F, Lovell, T, Hilgraf, R, Rostovtsev, VV, Noodleman, L, Sharpless, KB & Fokin, VV 2005, 'Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates', Journal of the American Chemical Society, vol. 127, no. 1, pp. 210-216. https://doi.org/10.1021/ja0471525
Himo, Fahmi ; Lovell, Timothy ; Hilgraf, Robert ; Rostovtsev, Vsevolod V. ; Noodleman, Louis ; Sharpless, K. Barry ; Fokin, Valery V. / Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 1. pp. 210-216.
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