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

Diverse and efficient catalytic applications of new cockscomb flower-like Fe3O4@SiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite in the environmentally benign reduction and reductive acetylation of nitroarenes and one-pot synthesis of some coumarin compounds

Morteza Hasanpour Galehban  1 , Behzad Zeynizadeh  1 , Hossein Mousavi  1
Affiliations

Diverse and efficient catalytic applications of new cockscomb flower-like Fe3O4@SiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite in the environmentally benign reduction and reductive acetylation of nitroarenes and one-pot synthesis of some coumarin compounds

Morteza Hasanpour Galehban et al. RSC Adv. .

Abstract

In this research, Fe3O4@SiO2@KCC-1@MPTMS@CuII 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 Fe3O4@SiO2@KCC-1@MPTMS@CuII 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-2H-chromen-2-ones) (namely, bis-coumarins) (3a-n) and 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles (6a-n) along with acceptable turnover numbers (TONs) and turnover frequencies (TOFs). Furthermore, the mentioned CuII-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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Catalytic applications of the cockscomb flower-like Fe3O4@SiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite in the reduction and reductive acetylation of nitroarenes in water and solvent-free one-pot synthesis of some coumarin compounds.
Scheme 1
Scheme 1. Preparation of the cockscomb flower-like Fe3O4@SiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite.
Fig. 2
Fig. 2. FT-IR spectra of the (a) Fe3O4, (b) Fe3O4@SiO2@KCC-1, (c) Fe3O4@SiO2@KCC-1@MPTMS, and (d) Fe3O4@SiO2@KCC-1@MPTMS@CuII nanosystems.
Fig. 3
Fig. 3. PXRD patterns of the (a) Fe3O4 and (b) Fe3O4@SiO2@KCC-1@MPTMS@CuII nanostructures.
Fig. 4
Fig. 4. SEM images of the cockscomb flower-like Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Fig. 5
Fig. 5. TEM images of the dendritic Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Fig. 6
Fig. 6. SEM-based EDX spectrum of the Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Fig. 7
Fig. 7. TGA/DTA diagram of the Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Fig. 8
Fig. 8. VSM diagram of the Fe3O4 NPs and Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Fig. 9
Fig. 9. UV-Vis spectra of the nanocomposite derived from the sources of Cu(NO3)2·6H2O, Cu2O, and Cu0.
Fig. 10
Fig. 10. Nitrogen (N2) gas adsorption–desorption profile of the as-prepared Fe3O4@SiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite.
Scheme 2
Scheme 2. Plausible mechanism of the one-pot reductive acetylation of nitroarenes catalyzed by the Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite in water.
Scheme 3
Scheme 3. Solvent-free one-pot pseudo-three-component synthesis of bis-coumarins (3a–n) catalyzed by the Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Scheme 4
Scheme 4. Solvent-free one-pot three-component synthesis of 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles (6a–n) catalyzed by the Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Scheme 5
Scheme 5. Plausible mechanism for the solvent-free one-pot pseudo-three-component synthesis of bis-coumarins (3a–n) catalyzed by the Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Scheme 6
Scheme 6. Plausible mechanism for the solvent-free one-pot three-component synthesis of 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles (6a–n) catalyzed by the Fe3O4@SiO2@KCC-1@MPTMS@CuII nanocomposite.
Fig. 11
Fig. 11. Recoverability and reusability experiments of the dendritic Fe3O4@SiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite.
Fig. 12
Fig. 12. TEM image of the recycled Fe3O4@SiO2@KCC-1@MPTMS@CuII mesoporous nanocomposite.
See this image and copyright information in PMC

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