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三乙醇胺-Cu(II)配合物在磁性碳纳米管上的固载作为一种有前途的可回收催化剂用于醛合成 5-取代 1H-四唑。

Anchoring of triethanolamine-Cu(II) complex on magnetic carbon nanotube as a promising recyclable catalyst for the synthesis of 5-substituted 1H-tetrazoles from aldehydes.

机构信息

Department of Chemistry, Semnan University, Semnan, 35131-19111, Iran.

出版信息

Mol Divers. 2020 May;24(2):319-333. doi: 10.1007/s11030-019-09951-6. Epub 2019 Apr 9.

Abstract

The development of heterogenization of copper nanoparticles on conductive supports is very challenging and has received much attention. Here, we synthesize a practical, efficient, and inexpensive heterogeneous catalyst to grow stable metallic copper(II) nanoparticles on the surface of magnetic carbon nanotube (FeO-CNT) catalyst support physically functionalized with triethanolamine (TEA) that acts as a low-cost and non-toxic ligand to capture the copper nanoparticles [FeO-CNT-TEA-Cu(II)]. The as-prepared heterogeneous catalyst was characterized by different techniques, such as Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, vibrating sample magnetometer, X-ray diffraction patterns, field-emission scanning electron microscopy, and atomic absorption spectroscopy analysis. The catalytic behavior of FeO-CNT-TEA-Cu(II) was investigated in the preparation of 5-substituted 1H-tetrazole derivatives via one-pot, three-component reaction between aromatic aldehydes, hydroxylamine, and sodium azide. The low catalyst loading, wide substrate scope, use of inexpensive materials, simple separation of the catalyst from the reaction mixture by an external magnet, short reaction times, easy workup, affordability, and superb yield are some advantages of this protocol.

摘要

在导电载体上实现铜纳米粒子的异质化发展极具挑战性,因此受到了广泛关注。在此,我们通过物理功能化三乙醇胺(TEA)合成了一种实用、高效且廉价的非均相催化剂,该催化剂可在经过三乙醇胺(TEA)功能化的磁性碳纳米管(FeO-CNT)催化剂载体表面生长稳定的金属铜(II)纳米粒子,TEA 作为一种廉价且无毒的配体可捕获铜纳米粒子[FeO-CNT-TEA-Cu(II)]。采用傅里叶变换红外光谱、能量色散 X 射线光谱、热重分析、振动样品磁强计、X 射线衍射图谱、场发射扫描电子显微镜和原子吸收光谱分析等多种技术对所制备的非均相催化剂进行了表征。通过一锅法、三组分反应,研究了 FeO-CNT-TEA-Cu(II) 在制备 5-取代 1H-四唑衍生物中的催化行为,该反应涉及芳香醛、羟胺和叠氮化钠。该方法具有催化剂用量低、底物适用范围广、使用廉价材料、通过外加磁铁从反应混合物中简单分离催化剂、反应时间短、后处理简单、经济实惠、产率高等优点。

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