Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand‐free click synthesis of diverse 1,2,3‐triazoles and tetrazoles

Abstract

Magnetic CuFe 2 O 4 /g-C 3 N 4 hybrids were synthesized through a facile method and their catalytic performances were evaluated in click chemistry for the first time. The structural and morphological characterization of prepared materials was carried out by different techniques such as X-ray diffraction, highresolution transmission electron microscopy, field emission scanning electron microscopy, Fourier infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, and N 2 adsorption-desorption analysis (Brunauer-Emmett-Teller surface area). The utilization of magnetic CuFe 2 O 4 /g-C 3 N 4 enabled superior performance in the one-pot azide-alkyne cycloaddition reaction in water using alkyl halides and epoxides as azide precursors without the need of any additional agents. The present system is broad in scope and especially practical for the synthesis of macrocyclic triazoles and also tetrazoles. In addition, the catalytic system highly fulfills the demands of "green click chemistry" with its convenient conditions, especially easy access to a variety of significant products in low catalyst loading and simple workup and isolation procedure.

Role of Click Chemistry in Organic Synthesis

“…The compound 21f possessed the highest activity [47]. In continuation to this, magnetic CuFe2O4/g-C3N4 hybrids were synthesized and their catalytic activity was examined in the synthesis of triazole derivatives (22 and 23) using terminal alkyne, azide, epoxide or haloarene (Figure 14) [48].…”

Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions

“…In this context, catalysts based on magnetic carbon materials have also been studied as CuAAC catalyst supports. In this respect, Khalili et al impregnated magnetic copper ferrite on mesoporous graphitic carbon nitride for the synthesis of the corresponding CuFe 2 O 4 /g-C 3 N 4 hybrids [155]. The magnetic nanocomposites showed excellent performance as heterogeneous catalysts in the one-pot azide-alkyne cycloaddition reaction between terminal alkynes and alkyl halides or epoxides azide precursors in water as a solvent at 80 • C. Moreover, the CuFe 2 O 4 /g-C 3 N 4 catalyst was able to be recovered and reused several times up to six catalytic cycles, with its main activity being retained (95-91%).…”

Copper(I) Complex of Dihydro Bis(2‐Mercapto Benzimidazolyl) Borate as an Efficient Homogeneous Catalyst for the Synthesis of 2H‐Indazoles and 5‐Substituted 1H‐Tetrazoles

“…Considering these outstanding features, [78][79][80] transition metal-scorpionate complexes have often been the homogeneous catalytic of choice and various applications such as CÀ H activations, aerobic oxidations, polymerizations, enzyme mimicry, and multicomponent reactions have been reported. [81][82][83][84][85] In this article and as part of our ongoing studies on the catalytic applications of copper complexes in the organic transformations, [86][87][88][89] we examined the effect of Cu(I) complexes with bipodal sulfur donor borate ligands based on 2mercaptobenzimidazole and different phosphine co-ligands as an effective homogeneous catalytic system for the formation of 2H-indazoles and 5-substituted 1H-tetrazoles. The sodium precursor complex of 2-mercaptobenzimidazole borate and its copper complexes are highly stable towards air and moisture.…”

“…In this article and as part of our ongoing studies on the catalytic applications of copper complexes in the organic transformations, [86–89] we examined the effect of Cu(I) complexes with bipodal sulfur donor borate ligands based on 2‐mercaptobenzimidazole and different phosphine co‐ligands as an effective homogeneous catalytic system for the formation of 2 H ‐indazoles and 5‐substituted 1 H ‐tetrazoles. The sodium precursor complex of 2‐mercaptobenzimidazole borate and its copper complexes are highly stable towards air and moisture.…”