Abstract
A supported gold nanoparticle-catalyzed strategy has been utilized to promote a click chemistry reaction for the synthesis of 1,2,3-triazoles via the azide-alkyne cycloaddition (AAC) reaction. While the advent of effective non-copper catalysts (i.e., Ru, Ag, Ir) has demonstrated the catalysis of the AAC reaction, additional robust catalytic systems complementary to the copper catalyzed AAC remain in high demand. Herein, Au nanoparticles supported on Al2O3, Fe2O3, TiO2 and ZnO, along with gold reference catalysts (gold on carbon and gold on titania supplied by the World Gold Council) were used as catalysts for the AAC reaction. The supported Au nanoparticles with metal loadings of 0.7–1.6% (w/w relative to support) were able to selectively obtain 1,4-disubstituted-1,2,3-triazoles in moderate yields up to 79% after 15 min, under microwave irradiation at 150 °C using a 0.5–1.0 mol% catalyst loading through a one-pot three-component (terminal alkyne, organohalide and sodium azide) procedure according to the “click” rules. Among the supported Au catalysts, Au/TiO2 gave the best results.
Highlights
Numerous efforts have been made to synthesize metal nanoparticles with controllable size and morphology which is pivotal in determining their catalytic properties [2], The catalytic use of nanostructured materials suspended in colloidal solutions, as well as those deposited on different supports for organic transformations, were highlighted in many studies [3,4,5]
In association with our research interest on the development of effective catalysts for the azide-alkyne cycloaddition (AAC) reaction, this current study presents the use of Au NPs supported on various the AAC reaction, this current study presents the use of Au NPs supported on various metal metal oxides as heterogenous catalysts
The catalytic activity of Au NPs deposited on different solid supports (Al2 O3, Fe2 O3, TiO2 and ZnO) in the microwave-assisted AuAAC reaction was investigated
Summary
Au catacatalysts [8,9], gold nanoparticles (Au NPs) have emerged as key materials in nanoscience lysts have applications in many reactions of industrial and ecological Au relevance [5,14,15]. C-O, C-N, and C-S bonds by nucleophilic on the impacted reactive by the preparation method, the nature of the support, and in particular, the size and shape multiple bonds [16,17] Their catalytic activity is significantly impacted by of the nanoparticles [5,15]. Reactions performed with gold catalysts have been reported, the Authe nanoparticles catalyzed cycloadditions (AuAAC), leading have to 1,4andreported, 1,5-disubstitutedWhile alkyne-azide many reactions performed with gold catalysts been the Au1,2,3- triazoles, have remained elusive(AuAAC),.
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