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  • Title: Metal-free 1,5-regioselective azide-alkyne [3+2]-cycloaddition.
    Author: Kloss F, Köhn U, Jahn BO, Hager MD, Görls H, Schubert US.
    Journal: Chem Asian J; 2011 Oct 04; 6(10):2816-24. PubMed ID: 21882350.
    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.
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