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Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates
KTH, School of Biotechnology (BIO), Theoretical Chemistry.
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2005 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 127, no 1, 210-216 p.Article in journal (Refereed) Published
Abstract [en]

Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(l) 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.

Place, publisher, year, edition, pages
2005. Vol. 127, no 1, 210-216 p.
Keyword [en]
click-chemistry, azide-alkyne, terminal alkynes, cycloaddition, ligation, exchange, route, acids, model
Identifiers
URN: urn:nbn:se:kth:diva-14455DOI: 10.1021/ja0471525ISI: 000226240900051OAI: oai:DiVA.org:kth-14455DiVA: diva2:332496
Note
QC 20100525Available from: 2010-08-05 Created: 2010-08-05Bibliographically approved

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