Metal-free Regioselective Azide-alkyne [3+2]-Cycloaddition in Water
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Kloß, Florian; Köhn, Uwe; Hager, Martin D.; Jahn, Burkhard O.; Görls, Helmar; Schubert, Ulrich S.
- Abstract:
- [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.
- Year:
- 2011
- Type of Publication:
- Article
- Journal:
- Chemistry – An Asian Journal
- Volume:
- 10
- Pages:
- 2816 - 2824