1073242-83-7Relevant articles and documents
1,3-Dipolar cycloaddition of organic azides to alkynes by a dicopper-substituted silicotungstate
Kamata, Keigo,Nakagawa, Yoshinao,Yamaguchi, Kazuya,Mizuno, Noritaka
, p. 15304 - 15310 (2008)
The dicopper-substituted γ-Keggin silicotungstate TBA 4[γ-H2SiW10O36Cu 2(μ-1,1-N3)2] (I, TBA = tetra-n- butylammonium) could act as an efficient precatalyst for the regioselective 1,3-dipolar cycloaddition of organic azides to alkynes. Various combinations of substrates (four azides and eight alkynes) were efficiently converted to the corresponding 1,2,3-triazole derivatives in excellent yields without any additives. The present system was applicable to a larger-scale cycloaddition of benzyl azide to phenylacetylene under solvent-free conditions (100 mmol scale) in which 21.5 g of the analytically pure corresponding triazole could be isolated. In this case, the turnover frequency and the turnover number reached up to 14 800 h-1 and 91 500, respectively, and these values were the highest among those reported for the copper-mediated systems so far. In addition, I could be applied to the one-pot synthesis of 1-benzyl-4-phenyl-1H-1, 2,3-triazole from benzyl chloride, sodium azide, and phenylacetylene. The catalyst effect, kinetic, mechanistic, and computational studies show that the reduced dicopper core plays an important role in the present 1,3-dipolar cycloaddition.
A highly efficient copper(i) catalyst for the 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes in water: Regioselective synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles
Garcia-Alvarez, Joaquin,Diez, Josefina,Gimeno, Jose
supporting information; experimental part, p. 2127 - 2130 (2011/02/21)
A new water soluble Cu(i) complex that exhibits a versatile and high catalytic activity in the Huisgen cycloadditions of azides and terminal alkynes in aqueous media under mild conditions is the first well-defined Cu(i) catalyst that is active with 1-iodo
