Copper-doped functionalized β-cyclodextrin as an efficient green nanocatalyst for synthesis of 1,2,3-triazoles in water

Abstract

The synthesis of 1,2,3-triazoles with immobilized Cu(I) in thiosemicarbazide-functionalized β-cyclodextrin (Cu@TSC-β‐CD) as a supramolecular catalyst was discussed. The catalyst was characterized by Fourier-transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), and Inductively Coupled Plasma Optical Emission Spectroscopy (ICP-OES) measurements. The catalyst showed high activity (up to 95% yields of triazole products under optimized reaction conditions), providing a one-pot, atom-economic, and highly regioselective green method for 1,2,3-triazoles synthesis in an azide-alkyne cycloaddition (AAC) protocol in water. High stability and no appreciable leaching of Cu(I) were observed, owing to its strong binding via the coordination with thiosemicarbazide functionality.

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

“…Naimi-Jamal and co-workers 78 reported a synthesis of 1,4-disubstituted triazoles 120 and 121 from 1 , azides 44/119 , and alkyl halides 118 using novel, stable, water-soluble, as well as homogeneous catalyst β-CD-TSC@Cu (copper(I) ions supported on functionalized β-cyclodextrin) as a supramolecular moiety in an aqueous medium with excellent regioselectivity and high yield ( Scheme 26 ). The catalyst was utilized up to 7 times without a remarkable loss of its activity.…”

Green catalytic synthesis of symmetric and non-symmetric β-hydroxy-1,2,3-triazoles by using epichlorohydrin in the presence of Cu(ii) coordination compounds containing oxazole ligands

“…The Huisgen 1,3-bipolar cycloaddition reaction involving alkynes and organic azides in the presence of copper catalysts is the simplest, effective and popular method for the synthesis of 1,2,3-triazoles. 9 The multi-component click reaction by using in situ generated organic azides has considerably solved the limitations and problems related to the use of organic azides in recent years. The reaction of alkyl halides with sodium azide is the main method for the in situ production of organic azides and has a high popularity.…”

Microwave-assisted catalyst-free multicomponent one-pot green synthesis of highly functionalized aminocyanopyridines and (4-hydroxy)quinolines in aqueous medium and its in silico studies

“…In the synthesis of aminocyanopyridine, water was used to enhance the rate of the reaction by Anderson 7,8 and Sharpless. [9][10][11][12][13] Various types of reactions including Knoevenagel condensation, [14][15][16][17][18][19][20] 1,3-dipolar cycloaddition, [21][22][23][24][25] oxidationreduction, [26][27][28] nucleophilic substitution, [29][30][31][32] aldol, [33][34][35][36] Michael addition, 18,37 cross-coupling, 38,39 and multi-component reactions 1 have been attempted in water for green synthesis. However, multicomponent reactions enjoy fast development and outstanding status in organic 40,41 and medicinal chemistry for a high degree of atom economy and diversity-oriented convergent synthesis 42 of organic molecules and biologically important molecules using simple and readily available substrates.…”