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New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine

[ Vol. 15 , Issue. 4 ]

Author(s):

Nitin Kore and Pavel Pazdera*   Pages 552 - 565 ( 14 )

Abstract:


Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene.

Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds.

Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting α-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole.

Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable, and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.

Keywords:

Polymer solid support, Supported Cu(I) catalyst, Click chemistry, Azide-Nitrile cycloaddition, recyclable green catalyst, green process.

Affiliation:

Centre for Syntheses at Sustainable Conditions and their Management, Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, CZ-62500 Brno, Centre for Syntheses at Sustainable Conditions and their Management, Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, CZ-62500 Brno

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