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Metal-Free 1,5-Regioselective Azide-Alkyne [3+2]-Cycloaddition
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
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2011 (English)In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 6, no 10, 2816-2824 p.Article in journal (Refereed) Published
Abstract [en]

[3+2]-cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5-disubstituted-4-(trimethyl-silyl)-1H-1,2,3-triazoles. The formation of the 1,5-isomer is highly favored in this metal-free cycloaddition, which could be proven by 1D selective NOESY and X-ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5-isomer. The described method provides a simple alternative protocol to metal-catalyzed "click chemistry" procedures, widening the scope for regioselective heavy-metal-free synthetic applications.

Place, publisher, year, edition, pages
2011. Vol. 6, no 10, 2816-2824 p.
Keyword [en]
alkynes, azides, click chemistry, cycloaddition, regioselectivity
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-161470DOI: 10.1002/asia.201100404ISI: 000296273900022OAI: oai:DiVA.org:uu-161470DiVA: diva2:456186
Available from: 2011-11-14 Created: 2011-11-14 Last updated: 2017-12-08Bibliographically approved

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Jahn, Burkhard O.

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