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

Mahdieh Tajbakhsh; Mohammad Reza Naimi-Jamal

doi:10.1038/s41598-022-08868-9

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

Sci Rep. 2022 Mar 23;12(1):4948. doi: 10.1038/s41598-022-08868-9.

Authors

Mahdieh Tajbakhsh¹, Mohammad Reza Naimi-Jamal²

Affiliations

¹ Research Laboratory of Green Organic Synthesis and Polymers, Department of Chemistry, Iran University of Science and Technology, P.O. Box 16846-13114, Tehran, Iran.
² Research Laboratory of Green Organic Synthesis and Polymers, Department of Chemistry, Iran University of Science and Technology, P.O. Box 16846-13114, Tehran, Iran. naimi@iust.ac.ir.

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.

MeSH terms

Copper* / chemistry
Spectroscopy, Fourier Transform Infrared
Triazoles
Water
beta-Cyclodextrins*

Substances

Triazoles
beta-Cyclodextrins
Water
Copper