Recyclable clay supported Cu (II) catalyzed tandem one-pot synthesis of 1-aryl-1,2,3-triazoles

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

“…On the other hand, Cu(II) species without deliberate addition of a reducing agent for CuAAC reactions have also been investigated. The mechanistic studies indicated that the real catalytic Cu(I) species were generated in a short induction period via reducing Cu(II) salts by alcoholic solvents [127], sodium azide [46,128], or thiobenzanilide [129] especially in the three-component 1,3-dipolar cycloaddition for 1,4-disubstituted 1,2,3-triazoles synthesis. For instance, the recently reported 2-pyrrolecarbaldiminato-Cu(II) complexes efficiently catalyzed three-component 1,3-dipolar cycloaddition reaction of benzyl halides and sodium azide with terminal alkynes in water at r.t., leading to the synthesis of several regioselective 1,4-disubstituted 1,2,3-triazoles in 55-97% yield [130].…”

One-pot three-component synthesis of 1,2,3-triazoles using magnetic NiFe2O4–glutamate–Cu as an efficient heterogeneous catalyst in water

“…2 The most popular method for the construction of the 1,2,3-triazole framework is Cu(I)-catalyzed 1,3-dipolar Huisgen cycloaddition reaction of azides with alkynes (CuAAC). 5 In order to overcome the difficulty of catalyst separation, some heterogenerous catalytic system have been developed, including Cu(II)-hydrotalcite, 6 Cu(I)-modified zeolite, 7 copper nanoparticles on activated carbon, 8 Cu(I)@phosphorated SiO 2 9 copper supported on the SiO 2 nanoparticle, 10 CuFe 2 O 4 magnetic nanoparticles 11 for the synthesis of β-hydroxy-1,2,3-triazoles, copper nanoparticles supported on agarose, 12 Cu(I) on waste oyster shell powder, 13 Fe 3 O 4 magnetic nanoparticle(MNP)-supported copper(I), 14 Cu(I) on charcoal, 15 copper nanoparticles supported on activated carbon, 16 nano ferrite-glutathione-copper (nano-FGT-Cu), 17 Cu(I) supported on alumina (Cu/Al 2 O 3 ), 18 polymer-supported copper, 19 Cu 2 O nanocubes, 20 copper immobilized onto a triazole functionalized magneticnanoparticle, 21 cellulose supported cuprous iodide nanoparticles, 22 supported CuBr on graphene oxide/Fe 3 O 4 , 23 Cu(II) PBS-bridged PMOs 24 for the synthesis of 1-alkyl-4-aryl-1,2,3-triazoles, and CuFe 2 O 4 nanoparticles, 25 Fe 3 O 4 nanoparticle-supported Cu(II)-β-cyclodextrin complex, 26 clay supported Cu(II) 27 for the synthesis of 1-aryl-1,2,3-triazoles. 4 To overcome this drawback, one-pot three-component methodologies for in situ generation of azides have been developed.…”

Regioselective synthesis of 1,2,3-triazoles catalyzed over ZnO supported copper oxide nanocatalyst as a new and efficient recyclable catalyst in water

“…Copper-based catalysts can perform the cycloaddition reaction of azides with terminal alkynes by Cu(I) and/or Cu(II) species. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Moreover, the performance of Ru-based catalysts on the cycloaddition of azides and terminal alkynes (RuAAC) for the regioselective synthesis of 1,2,3-triazoles has been reported. 26 Particularly, application of nano-metal oxides as catalysts in organic synthesis has been improved because of their significant characteristics.…”