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

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 language	English
Pages (from-to)	210-216
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	127
Issue number	1
DOIs	https://doi.org/10.1021/ja0471525
Publication status	Published - 12 Jan 2005
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1021/ja0471525

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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

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 journal › Article

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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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AU - Noodleman, Louis

AU - Sharpless, K. Barry

AU - Fokin, Valery V.

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