Research Laboratory of Green Organic Synthesis and Polymers, Department of Chemistry, Iran University of Science and Technology, P.O. Box 16846-13114, Tehran, Iran.
Sci Rep. 2022 Mar 23;12(1):4948. doi: 10.1038/s41598-022-08868-9.
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.
讨论了在硫代缩氨基脲功能化β-环糊精(Cu@TSC-β-CD)固定化 Cu(I) 作为超分子催化剂合成 1,2,3-三唑的方法。通过傅里叶变换红外光谱(FT-IR)、热重分析(TGA)、X 射线衍射(XRD)、扫描电子显微镜(SEM)、能谱(EDS)和电感耦合等离子体发射光谱(ICP-OES)对催化剂进行了表征。该催化剂表现出高活性(在优化反应条件下,三唑产物的产率高达 95%),提供了一种在水中通过叠氮-炔环加成(AAC)反应一锅法、原子经济性和高区域选择性的绿色方法合成 1,2,3-三唑。由于其通过与硫代缩氨基脲功能基的配位而具有强结合,因此观察到高稳定性和 Cu(I)的可忽略不计的浸出。