Copper Immobilized on Nanosilica Triazine Dendrimer (Cu(II)-TD@nSiO₂)-Catalyzed Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles and Bis- and Tris-Triazoles via a One-Pot Multicomponent Click Reaction

Abstract

An efficient, atom-economical, and regioselective synthesis of a wide range of 1,4-disubstituted 1,2,3-triazoles in excellent yields has been achieved via a one-pot three-component reaction of alkynes and sodium azide with organic halides or α-bromo ketones catalyzed by Cu(II)-TD@nSiO2/sodium ascorbate at room temperature. This catalytic system also showed excellent activity in the synthesis of bis- and tris-1,4-substituted 1,2,3-triazoles. Moreover, the catalyst could be recycled and reused for seven cycles without any loss in its catalytic activity.

Polystyrene-supported ionic liquid copper complex: A reusable catalyst for one-pot three-component click reaction

“…These results in combination with our efforts on the development of efficient copper catalysts for organic transformations [44][45][46], prompted us to report a green, convenient and regioselective method for synthesis of mono-and bis-1,4-disubstituted 1,2,3-triazoles in the presence of Cu(II) immobilized on polystyrene supported ionic liquid as a reusable catalyst (Scheme 1). …”

Copper-catalysed azide–alkyne cycloadditions (CuAAC): an update

“…101 Reactions were completed in fairly short times and the catalytic activity was not damaged after 7 subsequent runs.…”

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

“…[131] This heterogeneous catalyst system was well suited for the regioselective one-pot synthesis of mono-, bis, and tris-1,2,3-triazoles with a variety of different alkynes via in situ generation of alkyl azides using structurally varied alkyl halides (see also chapter 4). [131] This heterogeneous catalyst system was well suited for the regioselective one-pot synthesis of mono-, bis, and tris-1,2,3-triazoles with a variety of different alkynes via in situ generation of alkyl azides using structurally varied alkyl halides (see also chapter 4).…”

“…[131,158,159] The double CuAAC of azides with bis(triisopropylsilyl)butadiyne was shown to quickly furnish multidentate 1,1'-disubstituted 4,4'-bis(triazole) chelators 87, which were transformed into ruthenium complex 88 and studied with respect to the photophysical properties (Scheme 65). These types of ligands were employed to synthesize supramolecular Ag(I) and Cu(II) complex architectures 85 and 86 (Scheme 64).…”