1338916-51-0Relevant articles and documents
Metal-free 1,5-regioselective azide-alkyne [3+2]-cycloaddition
Kloss, Florian,Koehn, Uwe,Jahn, Burkhard O.,Hager, Martin D.,Goerls, Helmar,Schubert, Ulrich S.
, p. 2816 - 2824 (2012/06/01)
[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.