In the search for establishing a clickable copper-catalysed (3 + 2) Huisgen azide–alkyne cycloaddition (CuAAC) reaction under strict conditions, in particular in terms of preventing the presence of copper particles/traces in reaction products and using an environmentally benign medium such as water, we describe here the synthesis of an aminomethyl polystyrene-supported copper(I) catalyst (Cu(I)-AMPS) and its characterization by means of Fourier transform infrared and energy-dispersive X-ray spectroscopies and scanning electron microscopy. Cu(I)-AMPS was found to be highly active in the CuAAC reaction of various organic azides with alkynes affording the corresponding 1,4-disubstituted 1,2,3-triazoles in a regioselective manner in air at room temperature and using water as solvent. The insolubility and/or partial solubility of the organic azide and alkyne precursors as well as the heterogeneous Cu(I)-AMPS catalytic system points to the occurrence of the cycloaddition at the organic–water interface ‘on water’ affording quantitative yields of water-insoluble 1,2,3-triazoles. A mechanistic study was performed using density functional theory aiming at explaining the observed reactivity and selectivity of the Cu (I)-AMPS catalyst in CuAAC reactions.

A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study

De Munno, Giovanni;
2019

Abstract

In the search for establishing a clickable copper-catalysed (3 + 2) Huisgen azide–alkyne cycloaddition (CuAAC) reaction under strict conditions, in particular in terms of preventing the presence of copper particles/traces in reaction products and using an environmentally benign medium such as water, we describe here the synthesis of an aminomethyl polystyrene-supported copper(I) catalyst (Cu(I)-AMPS) and its characterization by means of Fourier transform infrared and energy-dispersive X-ray spectroscopies and scanning electron microscopy. Cu(I)-AMPS was found to be highly active in the CuAAC reaction of various organic azides with alkynes affording the corresponding 1,4-disubstituted 1,2,3-triazoles in a regioselective manner in air at room temperature and using water as solvent. The insolubility and/or partial solubility of the organic azide and alkyne precursors as well as the heterogeneous Cu(I)-AMPS catalytic system points to the occurrence of the cycloaddition at the organic–water interface ‘on water’ affording quantitative yields of water-insoluble 1,2,3-triazoles. A mechanistic study was performed using density functional theory aiming at explaining the observed reactivity and selectivity of the Cu (I)-AMPS catalyst in CuAAC reactions.
aminomethyl polystyrene; click chemistry; CuAAC reaction; DFT methods; heterogeneous catalysis; Chemistry (all); Inorganic Chemistry
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/292708
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