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. 2019 Apr 29;9(23):13112-13121.
doi: 10.1039/c9ra01249d. eCollection 2019 Apr 25.

Immobilized antimony species on magnetite: a novel and highly efficient magnetically reusable nanocatalyst for direct and gram-scale reductive-coupling of nitroarenes to azoarenes

Behzad Zeynizadeh  1 , Fariba Faraji  1
Affiliations

Immobilized antimony species on magnetite: a novel and highly efficient magnetically reusable nanocatalyst for direct and gram-scale reductive-coupling of nitroarenes to azoarenes

Behzad Zeynizadeh et al. RSC Adv. .

Abstract

In this study, magnetic nanoparticles of Fe3O4@SbF x from the immobilization of SbF3 on magnetite were synthesized. The prepared nanocomposite system was then characterized using scanning electron microscopy, Fourier transform infrared spectroscopy, X-ray diffraction, energy-dispersive X-ray spectroscopy, vibrating sample magnetometry and inductively coupled plasma optical emission spectroscopy. Next, the catalytic activity of Fe3O4@SbF x MNPs was highlighted by one-pot reductive-coupling of aromatic nitro compounds to the corresponding azoarene materials with NaBH4. The reactions were carried out in refluxing EtOH within 6-25 min to afford the products in high yields. The reusability of the Sb-magnetite system was also studied for 6 consecutive cycles without significant loss of catalytic activity. This synthetic protocol provided several advantages in terms of introducing a novel catalytic system based on antimony species for direct and gram-scale preparation of azoarenes from nitroarenes, low loading of the nanocatalyst, mild reaction conditions, using ethanol as a green and economic solvent and high yield of the products.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Scheme 1
Scheme 1. Synthesis of azoarenes catalyzed by NaBH4/Fe3O4@SbFx MNPs system.
Scheme 2
Scheme 2. Synthesis of magnetically nanoparticles of Fe3O4@SbFx.
Fig. 1
Fig. 1. FT-IR spectra of (a) Fe3O4 and (b) Fe3O4@SbFx MNPs.
Fig. 2
Fig. 2. SEM images of (a) Fe3O4 and (b) Fe3O4@SbFx MNPs.
Fig. 3
Fig. 3. EDX spectra of (a) Fe3O4 and (b) Fe3O4@SbFx MNPs.
Fig. 4
Fig. 4. XRD diffractograms of (a) Fe3O4 and (b) Fe3O4@SbFx MNPs.
Fig. 5
Fig. 5. N2 adsorption–desorption isotherm of Fe3O4@SbFx MNPs.
Fig. 6
Fig. 6. Magnetization curves of (a) Fe3O4 and (b) Fe3O4@SbFx MNPs.
Scheme 3
Scheme 3. Reductive-coupling of nitrobenzene to azobenzene with NaBH4/Fe3O4@SbFx MNPs.
Scheme 4
Scheme 4. The proposed mechanism for reductive-coupling of nitroarenes to azoarenes with NaBH4/Fe3O4@SbFx system.
Fig. 7
Fig. 7. Reusability of Fe3O4@SbFx MNPs in reductive-coupling of PhNO2 with NaBH4.
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