Abstract

This works evaluates the catalytic capacity of metalorganic materials synthesized, based on Cu+ and ambidentade ligand in Huisgen cycloaddition reaction. The synthesis of 1,2,3-triazole was made using CuCl and CuI salts, and the [Cu(4,4’-dipy)]Cl and [Cu(4,4’-dipy)]I compounds as catalysts, with or without base catalysis by triethylamine. The copper salts and compounds lead to formation of the desired triazole product; however, in the synthesis mediated by [Cu(4,4’-dipy)]I does not generate the product, even after 48 h of reaction. The reaction with [Cu(4,4’-dipy)]Cl mediated or not by triethylamine showed high yields of 88 % and 70 %, respectively. The [Cu(4,4’-dipy)]Cl compounds was reused five times, and regenerated by ascorbic acid, maintaining thus, the same reaction yield.

Highlights

  • Metalorganic materials have attracted attention owing to their potential applications in gas separation and storage[1], as sensors[2], in drug storage and delivery[3], templated low-dimensional material preparations[4], and principally, as catalysts[5]

  • This works evaluates the catalytic capacity of metalorganic materials synthesized, based on Cu+ and ambidentade ligand in Huisgen cycloaddition reaction

  • The literature reports on several works that describe very recently the use of metalorganic materials as catalysts in solid-phase organic reactions, such as in Friedel– Crafts alkylation and acylation[6,7,8], oxidation[9,10,11,12,13,14], alkene epoxidation[15,16,17], hydrogenation[18], Suzuki cross-coupling[19, 20], the Sonogashira reaction[21], transesterification reaction[22], the Knoevenagel condensation[23,24,25], aldol condensation[26, 27] and 1,3dipolar cycloaddition reactions[28]

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Summary

Introduction

Metalorganic materials have attracted attention owing to their potential applications in gas separation and storage[1], as sensors[2], in drug storage and delivery[3], templated low-dimensional material preparations[4], and principally, as catalysts[5] Due to their high surface areas, pore sizes, ease and diversity of their ability to process, these compounds can be used in catalysis. The copper(I) catalyst promotes the formation of 1,2,3-triazoles from azides and terminal alkynes, with high yields, mild conditions and excellent regioselectivity[30, 31] In this reaction, the desired product is isolated by chromatography and the copper(I) residues are removed by an extraction process, using successive washes with ammonium hydroxide[32, 33]

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