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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.
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Metadata
- Authors
- Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V. V., Noodleman, L., Sharpless, K. B., & Fokin, V. V.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-12-08
- Volume
- 127
- Issue
- 1
- Pages
- 210-216
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1988066093
- Cited by
- 1,738
- References
- 17
- FWCI
- 23.30
- Type
- journal article
- Language
- en
- Open access
- closed
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