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新型鸡冠花状FeO@SiO@KCC-1@MPTMS@Cu介孔纳米复合材料在硝基芳烃的环境友好型还原和还原乙酰化以及一些香豆素化合物的一锅法合成中的多样且高效的催化应用。

Diverse and efficient catalytic applications of new cockscomb flower-like FeO@SiO@KCC-1@MPTMS@Cu mesoporous nanocomposite in the environmentally benign reduction and reductive acetylation of nitroarenes and one-pot synthesis of some coumarin compounds.

作者信息

Hasanpour Galehban Morteza, Zeynizadeh Behzad, Mousavi Hossein

机构信息

Department of Organic Chemistry, Faculty of Chemistry, Urmia University Urmia Iran

出版信息

RSC Adv. 2022 Apr 20;12(18):11164-11189. doi: 10.1039/d1ra08763k. eCollection 2022 Apr 7.

Abstract

In this research, FeO@SiO@KCC-1@MPTMS@Cu as a new cockscomb flower-like mesoporous nanocomposite was prepared and characterized by various techniques including Fourier transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), SEM-based energy-dispersive X-ray (EDX) spectroscopy, inductively coupled plasma-optical emission spectrometry (ICP-OES), thermogravimetric analysis/differential thermal analysis (TGA/DTA), vibrating sample magnetometry (VSM), UV-Vis spectroscopy, and Brunauer-Emmett-Teller (BET) and Barrett-Joyner-Halenda (BJH) analyses. The as-prepared FeO@SiO@KCC-1@MPTMS@Cu mesoporous nanocomposite exhibited satisfactory catalytic activity in the reduction and reductive acetylation of nitroarenes in a water medium and solvent-free one-pot synthesis of some coumarin compounds including 3,3'-(arylmethylene)bis(4-hydroxy-2-chromen-2-ones) (namely, bis-coumarins) (3a-n) and 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4-chromene-3-carbonitriles (6a-n) along with acceptable turnover numbers (TONs) and turnover frequencies (TOFs). Furthermore, the mentioned Cu-containing mesoporous nanocatalyst was conveniently recovered by a magnet from reaction environments and reused for at least seven cycles without any significant loss in activity, which confirms its good stability.

摘要

在本研究中,制备了FeO@SiO@KCC-1@MPTMS@Cu这种新型鸡冠花状介孔纳米复合材料,并通过多种技术对其进行了表征,这些技术包括傅里叶变换红外(FT-IR)光谱、粉末X射线衍射(PXRD)、扫描电子显微镜(SEM)、透射电子显微镜(TEM)、基于SEM的能量色散X射线(EDX)光谱、电感耦合等离子体发射光谱(ICP-OES)、热重分析/差热分析(TGA/DTA)、振动样品磁强计(VSM)、紫外可见光谱以及布鲁诺尔-埃米特-特勒(BET)和巴雷特-乔伊纳-哈伦达(BJH)分析。所制备的FeO@SiO@KCC-1@MPTMS@Cu介孔纳米复合材料在水介质中对硝基芳烃的还原和还原乙酰化反应以及在无溶剂一锅法合成一些香豆素化合物(包括3,3'-(芳基亚甲基)双(4-羟基-2-色烯-2-酮)(即双香豆素)(3a-n)和2-氨基-4-芳基-7, ,7-二甲基-5-氧代-5,6,7,8-四氢-4-色烯-3-腈(6a-n))中表现出令人满意的催化活性,同时具有可接受的转化数(TONs)和转化频率(TOFs)。此外,上述含铜介孔纳米催化剂可通过磁铁方便地从反应环境中回收,并重复使用至少七个循环,活性无任何显著损失,这证实了其良好的稳定性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e7c/9020196/df44072d3699/d1ra08763k-f1.jpg

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