Robust and fast oxidation of sulfides by immobilized Mo(VI) complex on magnetic nanoparticles in solvent-free condition

Article abstract of DOI:10.1016/j.poly.2020.114382

In this research, a heterogeneous catalyst by modifying the magnetically reusable manganese ferrite nanomaterials with oxo-peroxomolybdenum (VI) Schiff base complex was prepared. The prepared catalyst was characterized completely using different physicochemical methods. The recoverable heterogeneous catalyst was tested with different sulfides for the sulfoxidation process under solvent-free situation. The significant and superior turnover frequency (TOF) of the nanocatalyst was acquired to oxidize C₇H₈S compound (9408 h^?1). The offered nanocatalyst has been shown catalytic selectivity, activity, and reusability in a short time. Furthermore, the heterogeneous catalyst has good recoverability at least five consecutive cycles without losing its selectivity towards products in the oxidation reaction.

Full text of DOI:10.1016/j.poly.2020.114382

Journal Pre-proofs
Robust and fast oxidation of sulfides by immobilized Mo(VI) complex on mag-
netic nanoparticles in solvent-free condition
Behnam Babaei, Abolfazl Bezaatpour, Hadi Basharnavaz
PII:
S0277-5387(20)30039-5
DOI:
https://doi.org/10.1016/j.poly.2020.114382
POLY 114382
Reference:
Polyhedron
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Revised Date:
Accepted Date:
17 October 2019
7 January 2020
17 January 2020
Please cite this article as: B. Babaei, A. Bezaatpour, H. Basharnavaz, Robust and fast oxidation of sulfides by
immobilized Mo(VI) complex on magnetic nanoparticles in solvent-free condition, Polyhedron (2020), doi: https://
doi.org/10.1016/j.poly.2020.114382
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Robust and fast oxidation of sulfides by immobilized Mo(VI) complex on magnetic
nanoparticles in solvent-free condition
Behnam Babaeia, Abolfazl Bezaatpoura,*1 and Hadi Basharnavaza
Department of Chemistry, Faculty of Basic Science, University of MohagheghArdabili 179,
Ardabil, Iran
Abstract
In this research, a heterogeneous catalyst by modifying the magnetically reusable
manganese ferrite nanomaterials with oxo-peroxomolybdenum (VI) Schiff base complex was
prepared. The prepared catalyst was characterized completely using different physicochemical
methods. The recoverable heterogeneous catalyst was tested with different sulfides for the
sulfoxidation process under solvent-free situation. The significant and superior turnover
frequency (TOF) of the nanocatalyst was acquired to oxidize C7H8S compound (9408 h-1). The
offered nanocatalyst has been shown catalytic selectivity, activity, and reusability in a short time.
Furthermore, the heterogeneous catalyst has good recoverability at least five consecutive cycles
without losing its selectivity towards products in the oxidation reaction.
Keywords:
Heterogeneous catalyst; Oxidation; Oxo-peroxomolybdenum; Solvent- free condition; Sulfide.
*Corresponding authrs:
E-mail address: a_bezaatpour@yahoo.com

Introduction
In the past decade, the conversion of organic compounds to useful oxidation products and
important chemical intermediates by transition metals are developed by researchers [1-4].
Among transition metal complexes, molybdenum (VI) complexes owing to several excellent
advantages including inexpensive, environmentally friendly, and highly efficient utilized as
catalysts for oxidation of organosulfur materials [2, 5, 6]. There is a multitude of reports about
selective oxidation of sulfide to sulfoxide [7-10]. Sulfoxides are known as one of the valuable
intermediates for the synthesis of useful materials such as drugs [9, 11], antifungal agents [12],
oxo-transfer reagents, chiral auxiliaries, intermediates of biologic molecules, and also very useful
in the activation of enzymes [13]. Even though great researches have been published in sulfides
to sulfoxides, unfortunately, most of them suffer from over oxidation to sulfone, low yields and
selectivity of products and expensive reagents (solvents). The use of chemical solvents in large
quantities is neither economically or environmentally suitable. Solvent-free condition reactions
are essential with big advantages including human health, considerable contributions to the
conservation of the environment, cost efficiency, and reducing of waste [8, 14, 15]. As literature
reports, the use of aqueous H2O2 as the greenest oxidizing agent is greatly preferred owing to its
very effective O content (30%) and sanitation as it produces only drinking H2O as a by-product
[16-18]. The recovering of the homogeneous catalyst from the products after the reaction is often
difficult, high costs, and causes extra waste. Moreover, insufficient thermal and chemical
stability, and also recycling of catalyst remains a scientific challenge [19]. Hence, supporting of
metal materials on the metal oxides has been attracted the attention of researchers in catalytic
fields [5, 20-22]. Recently, magnetite nanomaterials have been utilized strongly for this purpose,
because the magnetic nanomaterials have unique features including readily available, separate-

ability, the high surface area, biocompatibility, and low toxicity [23-29]. In the following of our
researches in catalyst [2, 3, 8, 20, 30-37], in this research, were ported on the preparation of
Mo(VI) complexes integrated onto modified manganese iron oxide. This nanocatalyst was
characterized by different methods and examined for the sulfoxidation process without the utilize
of any extra solvent.
2.1. Materials
2-Hydroxy-5-nitrobenzaldehyde, 2-hydroxy-benzaldehyde, 3-aminopropyltrimethoxy
silane (APTMS), MnCl2.4H2O, FeCl3.6H2O, diphenyl sulfide, thioanisole, dipropyl sulfide,
bis(4-hydroxyphenyl) sulfide, dimethyl sulfide, benzyl phenyl sulfide, diallyl sulfide,
benzothiophene, dibutyl sulfide, hydrogen peroxide (30%), chlorobenzene, MoO3, and NH3
(25%[w/w]) were provided from Sigma Aldrich Company.
2.2. Preparation of MFO@NH2
MnFe2O4 (MFO) nanomaterials were prepared according to Ref [38]. Briefly, an aqueous
solution (100 mL) of MnCl2.4H2O (0.1 M) and FeCl3.6H2O (0.2 M) was prepared added
dropwise into 100 mL NaOH (3 M) at 95 oC. The solution was stirred for 2 hours and the formed
precipitate collected, washed with deionized H2O, followed by ethanol and dried at 60 oC for 12
hours. Furthermore, 2g of the formed MnFe2O4 were dispersed in C2H5OH (50 mL) under ultra-
sonication and concentrated ammonia (2 mL) and 3-aminopropyltriethoxysilane (5 mL) were
o
added. It should be noted that this mixture was stirred at 80 C for 48 hours. The resulting
MFO@NH2 particles were collected by a permanent magnet. The MFO@NH2 materials were
washed two times with H2O and C2H5OH and also dried at 80 oC for 24 hours.

2.3. Preparation of MFO@NS
A solution of 5-nitro-salicylaldehyde (5 mmol, 0.8356 g dissolved in 50 mL C2H5OH)
was added dropwise to MFO@NH2 materials in C2H5OH (50 mL) and the suspension mixture
refluxed for 24 hours. The formed MFO@NS materials were collected by a magnet, and washed
two times with C2H5OH and also dried at 80 oC for 12 hours.
2.4. Preparation of MFO@NS-MoOO2
The catalyst was prepared by dissolving MoO3 (5.02 g, 35 mmol) in hydrogen peroxide
o
(30%, 70 mL) and stirring at 25 C for 24 hours. The mixture was filtered and this filtrated
solution was added dropwise to a suspension of MFO@NS (2 g in 50 mL of C2H5OH) and also
o
stirred at 80 C for 48 hours. The formed MFO@NS-MoOO2 materials were collected using a
o
magnet, washed two times with C2H5OH and dried at 80 C for 12 hours. Atomic ratio (calc;
obtained from X-ray photoelectron spectrum (XPS)): Fe/Mn, (2; 2.02); Mo/Si, (0.5; 0.49); Mo/N,
(0.25; 0.25)
2.5. Catalytic experiment
The following procedure is typical to 5 mg (0.00127 mmol based on molybdenum
characterized by XPS) of MFO@NS-MoOO2, sulfides (1 mmol), chlorobenzene (1 mmol) as
internal standard was added H2O2 (30% aqueous) (1.5 mmol). The catalytic reactor was stirred
o
for 5 min at 55 C and this nanocatalyst was separated using an external magnet force and the
reaction progress was monitored by gas chromatography.
3. Result and discussion

3.1. Preparation and characterization of heterogeneous catalyst
The MFO@NS-MoOO2 nanocatalyst was synthesized in a two-step manner by the first
preparation of the MnFe2O4 nanomaterials in a chemical co-precipitation process [38] followed
by amination with APTES and treatment of it with 2-hydroxy-5-nitrosalycilaldehyde and second
using complexation with Mo(O2)O compound (Scheme 1). Furthermore, Fig. 1 shown the FT-IR
spectroscopic analysis of MnFe2O4, MFO@NH2, MFO@NS, and MFO@NS-MoOO2
nanomaterials. By referring to Fig. 1a, vibration bands at 630 and 490 cm-1 are assigned,
respectively, for the Fe–O and Mn‒O bonds of the MnFe2O4 materials [39]. The vibration band
at 1116 cm−1 (Fig. 1b) is assigned to the Si-O‒Si bond in MnFe2O4@NH2 materials. So, the
MFO@NS particles in Fig. 2c illustrate in addition vibrations of the C=N stretching band at 1635
cm-1, while this band in MFO@NS-MoOO2, moves to a lower frequency and emerges at 1622
cm-1. Finally, as shown in Fig. 1d, the two nearby bands at 906 and 920 cm-1 are indicated of the
presence of symmetric and asymmetric stretches of the MoO(O2) group.
[Scheme 1]
[Figure 1]
Figure 2 displays the XRD patterns of the prepared (a) manganese iron oxide and (b)
MFO@NS-MoOO2 nanomaterials. The observed XRD patterns display the MnFe2O4
nanoparticles (with 2θ= 30.19º, 35.54º, 43.22º, 53.60º, 57.07º, 62.66º, and 71.15º corresponding
to the Bragg reflections from the (220), (311), (400), (422), (511), (440), and (533) planes,
respectively) are in a cubic structure with the standard pattern for JCPDS Card No. 89-4319.
[Figure 2]
Figure 3 shows the XPS of MFO@NS-MoOO2. From the X-ray photoelectron scrutiny
spectrum (Fig. 3a), bands at 529 (O 1s), 100 (Si 2p), 400 (N 1s), 709.8 eV (Fe 2p), 235 eV (Mo

3d), and 285 eV (C 1s) are observed with atomic percent for O, 51.14; N, 20.84; Mn, 0.96; Fe,
1.92; Mo, 5.21; and C, 17.67 and (Mo/N)=0.2; (Mo/Si)=0.5; and (Fe/Mn)=2, confirming that the
molybdenum Schiff base complex was unified onto the manganese iron oxide surface. The Mo
3d core level spectrum (Fig. 3c) displays the predominant Mo 3d5/2 and 3d3/2 peaks at 235.8 and
232.6 eV characteristic for Mo(VI). As illustrated in Fig. 3b, the O 1s core-level spectrum can be
divided into three bands: oxo-oxygen (530.1 eV), peroxo oxygen [40] (532.8 eV), and Mn‒O,
Fe‒O grafting in MnFe2O4 (531.6 eV).
[Figure 3]
The EDX spectra (Fig. 4) and EDX mappings of Fe Kα, Si Kα, Mn Kα, N Kα, and Mo Lα
of MFO@NS-MoOO2 nanomaterials (Fig. 4A, 4B, 4C, 4D, 4E, and 4F). The energy-dispersive
X-ray provided the presence of atoms including O, Mn, Fe, Si, Mo, N, and C, in good agremeent
with the chemical composition of the catalyst.
[Figure 4]
The size and morphology of MFO@NS-MoOO2 was evaluated by TEM and SEM and also
corresponding images are illustrated in Fig. 5. It is observed from the SEM image that no change
morphology between MFO@NS-MoOO2 (Fig. 5a) and MnFe2O4 materials (Fig. 5b) is observed,
and materials retained regular seamlessly shape. Furthermore, Fig. 5c indicates TEM images of
MFO@NS-MoOO2 nanocatalyst, displaying nanoparticles with an average size of about 10-15
nm.
[Figure 5]
The magnetic properties of MFO@NS-MoOO2 are illustrated in Fig. 6. The MFO@NS-
MoOO2 displays a small hysteresis loop with magnetic saturation at 31.01 emu/g. Furthermore,

as observed in Fig. 6, the MFO@NS-MoOO2 as a catalyst can still be separated from the solution
by an external magnetic.
[Figure 6]
3.2. Oxidation of sulfides
Oxidation of various sulfides was done using MFO@NS-MoOO2 as a catalyst and 30%
H2O2 as oxidant. Initially, in order to a determination of optimal catalyst was optimized different
parameters such as an amount of the catalyst, kind of solvent, temperature of the reaction, the
molar ratio of oxidant to the substrate and reaction time by thioanisole as a model reaction.
During optimizing the condition, it has been found that the best sulfoxidation results obtained
with the highest conversion (99%) during 5 min in solvent-free condition (Fig. 7). It appears that
significantly decreasing the catalytic activity in the present solvents related to the coordination of
solvents to Mo (VI). As presented in Fig. 8, the optimal temperature of catalytic activity acquired
o
at 55 C. It seems that with increasing temperature in the catalytic process decomposition of
H2O2 occurred. To improve the catalytic activity process and decreasing by products, several
molar ratio of [oxidant]/[substrat] were examined at the ranges of 0.5‒5 in the separate catalytic
reaction under solvent-free condition. As evident from Fig. 9, it has been found that the excellent
result for sulfoxidation reactions was obtained in 1.5 molar ratio [H2O2]/[methyl phenyl sulfide].
It seems that with increasing molar ratio of [H2O2]/[methyl phenyl sulfide] more than 1.5 caused
sulfone product. To determine the optimal amount of catalyst for the sulfoxidation process were
used several amounts of MFO@NS-MoOO2 including 0.5, 0.6, 0.7, 0.8, and 0.9 mg. The optimal
amount of catalyst for oxidation of C7H8S compound was acquired 0.5 mg (Fig. 10).
[Figure 7]

[Figure 8]
[Figure 9]
[Figure 10]
After optimizing the conditions, the generality of this method was examined for selective
oxidation of various sulfides using H2O2 (30%) as oxidant. The results are summarized in Table
1. It seems that alkyl and aryl sulfides are slightly more reactive than aromatic sulfides in the
sulfoxidation process. The prepared catalyst was separated easily using an external magnetic
field and utilized 5th times for subsequent sulfoxidation reactions. As for offering in Fig. 11, the
amounts of oxidation conversion of reactions are acceptable at least for 5th time. The DRS and
FT-IR spectra before and after the oxidation process indicated good physical-chemical stability
of the catalyst. (See Fig. 12a, b). The results of Table 2 [41-45] indicated that the merit of this
simple catalytic for sulfoxidation of thioanisole as a model substrate, in comparison with the
several catalysts in terms of catalyst loading, conversion rate, oxygen source, and especially,
conditions used in the reactions. Furthermore, from Table 2, it can be found that the catalytic
activity of Mo-based compound is significantly increased in comparison with the other metal-
based compounds because the active sites and adaptable nature of Mo-based compound is more
than those of the other compounds [46]. Inattention to the mechanism in Scheme 2, it seems that
the proposed mechanism in both oxidation catalytic proceeds via a seven‐coordinate
intermediate. In catalytic cycles, the oxidation process begins with attacking of oxidants to
molybdenum center and creation of oxoeperoxomolybdenum (VI) precursor. In the continuous,
substrate electron pair attacks the σ anti-bonding (O-O) of dioxoMo (VI), and finally, with the
production of products, the catalyst is regenerated.
[Figure 11]

[Figure 12]
[Scheme 2]
[Table 1]
[Table 2]
4. Conclusion
In summary, we studied the sulfoxidation reactions of different sulfides under solvent-free
condition using oxo-peroxo Mo complex supported over manganese iron oxide magnetic
nanoparticles. The MFO@NS-MoOO2 material shows a remarkable shorter catalytic reaction
time and excellent catalytic activity. The nanocatalyst was simply recovered successfully by
external magnetic from the mixture reaction and reused as a catalyst for 5 times without a
significant reducing of catalytic activity. Based on these resulrs, it can be deduced that the
heterogeneous catalyst has good recoverability at least five consecutive cycles without losing its
selectivity towards products in the oxidation reaction.

Scheme1.Preparation of MFO@NS-MoOO2 as novel heterogeneous nanocatalyst.
Figure 1. FT‐IR spectra of (a) MnFe2O4 (MFO) nanoparticles, (b) MFO@NH2, (c)MFO@NS, and (d)
MFO@NS-MoOO2 nanoparticles.

Figure 2. XRD patterns of (a) MFO@NS-MoOO2 and (b) MnFe2O4 (MFO) nanoparticles.

Figure 3. XPS survey spectrum of (a) MFO@NS-MoOO2, (b) core level spectra of O 1s, and (c) Mo 3d.

Figure 4. EDAX spectrum of MFO@NS-MoOO2 with the quantitative data. Insets show the SEM image
of the catalyst (a) elemental maps of an aggregate using (b) Mn Kα, (c) Fe Kα, (d) Si Kα, (e) N Kα, and
(f) Mo Lα.

Figure 5. SEM images of (a) MnFe2O4 (MFO), (b) MFO@NS-MoOO2, and (c) TEM images of
MFO@NS-MoOO2 nanoparticles.
Figure 6. Magnetization curves for (a) the MnFe2O4 (MFO), (b) MFO@NS-MoOO2, and (c) MFO@NS-
MoOO2 nanoparticles after 5th run.

Figure 7. Oxidation of thioanisole (1 mmol) in various solvents (5 mL) and under solvent-free condition
with 30% H2O2 (1.5 mmol) with MFO@NS-MoOO2 (1.251×10-3 mmol) during 5 min.
Figure 8. Optimization of catalytic reaction temperature, thioanisole (1 mmol), 30% H2O2 (1.5 mmol),
catalyst (1.251×10-3 mmol), solvent-free conditions, 5 min.

Figure 9. The effect of [H2O2] /[thioanisole] ratio on sulfoxidation conversion at 55 oC in
solvent-free condition, catalyst (0.00125 mmol), reaction time=5 min.
Figure 10. Effect of catalyst amount on sulfoxidation conversion (column) in solvent-free condition,
sulfide (1 mmol), H2O2 (1.5 mmol), T = 55 oC, reaction time = 5 min and decomposition of H2O2 (dashed)
T= 55 oC, reaction time = 5 min.

Figure 11. Cycling experiments, reaction conditions: solvent-free, thioanisole (1 mmol), H2O2 (30%
aqueous) (1.5 mmol), T=55 oC, reaction time = 5 min.

Figure 12. (a) DRS and (b) FT-IR spectra of the catalyst before (solid line) and after the 5th catalytic run
(dashed line)

Scheme 2. Proposed mechanism for catalytic oxidation of sulfides by the MFO@NS-MoOO2 in solvent-
free condition.

Table 1. Results of catalytic oxidation of various sulfides with H2O2 (30% aqueous) catalyzed by
MFO@NS-MoOO2.a
Sulfides
Conversion%b
(Reaction time)
Sulfoxide
Selectivity (%)
TOFc(h-1)
Oxidation product
98 (5 min)
99≤ (5 min)
98 (5 min)
98 (5 min)
60 (5 min)
≤2(5 min)
9 (5 min)
95
9408
100
100
100
100
100
100
100
100
9504
9408
9408
5760
192
864
70 (5 min)
d99≤ (5min)
6720
9504
a Catalytic reaction condition: solvent free; [H2O2]:[sulfides] (1.5:1), Catalyst = 0.00125 mmol, Reaction temperature = 55 ◦C.
b Conversion were determined by GC, Conversion = [mole of S]/[(mole of SO)+(mole of SO2)].
c Calculated as [mmol of product]/[mmol of catalyst]×hours

d Yield are quantitative on the basis of sulfide and refer to TLC yields and Isolated
Table 2. Comparison of literature reports on the oxidation of thioanisole under various conditions
Catalyst
substrate
Reaction conditions
Conversion (%)
Ref.
[MRAMoO2(O2)]
Thioanisole
H2O2(30%)/ Methanol/ 15 min
99
[41]
TiO2/AA/MoO2
Fe3O4@chit-based Cu complex
SBA–15 + ImCl + MoO5
Ti-MCM-41
Thioanisole
Thioanisole
Thioanisole
Thioanisole
H2O2(30%)/ Ethanol/ 30min
H2O2(30%)/ Solvent-free/ 90min
H2O2(30%)/ Methanol/ 60min
H2O2(30%)/ Solvent-free/ 120min
100
97
[42]
[43]
[1]
95
89
[44]
Mo-DAPSH@APTES@SiO2
Thioanisole
H2O2(30%)/ Solvent-free/ 30min
100
[45]
MFO@NS-MoOO2
Thioanisole
H2O2(30%)/ Solvent-free/ 5min
98
This work
Reference
[1] C.J. Carrasco, F. Montilla, L. Bobadilla, S. Ivanova, J.A. Odriozola,A. Galindo, Catal. Today, 255
(2015) 102-108.
[2] A. Bezaatpour, S. Khatami,M. Amiri,RSC. Adv, 6 (2016) 27452-27459.
[3] A. Bezaatpour, React. Kinet. Mech. Cat, 112 (2014) 453-465.
[4] T. Chattopadhyay, A. Chakraborty, S. Dasgupta, A. Dutta, M. I. Menendez, E. Zangrando, Appl.
Organomet. Chem, 31 (2017) 3663-3674.
[5] M. Bagherzadeh, M. Zare, J. Coord. Chem, 66 (2013) 2885-2900.
[6] M. Mirzaee, B. Bahramian,A. Amoli,Appl. Organomet. Chem, 29 (2015) 593-600.
[7] G. Romanowski, J. Kira, Polyhedron, 117 (2016) 352-358.
[8] A. Bezaatpour, E. Askarizadeh, S. Akbarpour, M. Amiri, B. Babaei, Mol. Catal, 436 (2017) 199-209.
[9] N. Baig, V. K. Madduluri, A. K. Sah, RSC. Adv, 6 (2016) 28015-28022.
[10] I. Tarkhanova, A. Anisimov, S. Verzhichinskaya, A. Buryak, V. Zelikman,M. Gantman, Petrol.
Chem, 56 (2016) 158-165.
[11] A. Rostami, B. Tahmasbi, F. Abedi, Z. Shokri, J. Mol. Catal. A: Chem, 378 (2013) 200-205.
[12] M. Madesclaire, Tetrahedron, 42 (1986) 5459-5495.
[13] R. Bentley, Chem. Soc. Rev, 34 (2005) 609-624.
[14] M. A. Martins, C. P. Frizzo, D. N. Moreira, L. Buriol, P. Machado, Chem. Rev, 109 (2009) 4140-
4182.

[15] Y. Kon, T. Yokoi, M. Yoshioka, S. Tanaka, Y. Uesaka, T. Mochizuki, K. Sato,T. Tatsumi,
Tetrahedron, 70 (2014) 7584-7592.
[16] S. Caron, R. W. Dugger, S. G. Ruggeri, J. A. Ragan, D. H. B. Ripin, Chem. Rev, 106 (2006) 2943-
2989.
[17] A. Podgorsek, M. Zupan, J. Iskra,Angew. Chem. Int. Edit, 48 (2009) 8424-8450.
[18] R. Noyori, M. Aoki, K. Sato, Chem. Commun, (2003) 1977-1986.
[19] R. Dileep, B. Rudresha, RSC. Adv, 5 (2015) 65870-65873.
[20] A. Bezaatpour, M. Amiri,V. Jahed, J. Coord. Chem, 64 (2011) 1837-1847.
[21] L. Hamidipour, F. Farzaneh, C.R. Chim, 17 (2014) 927-933.
[22] C. Baleizao, B. Gigante, D. Das, M. Alvaro, H. Garcia,A. Corma, J. Catal, 223 (2004) 106-113.
[23] C.I. Fernandes, M.D. Carvalho, L.P. Ferreira, C.D. Nunes, P.D. Vaz, J. Organomet. Chem, 760
(2014) 2-10.
[24] A. Farokhi, H. Hosseini-Monfared, New. J. Chem, 40 (2016) 5032-5043.
[25] J. Sun, G. Yu, L. Liu, Z. Li, Q. Kan, Q. Huo, J. Guan,Cat. Sci. Tec, 4 (2014) 1246-1252.
[26] X. Zhang, G. Wang, M. Yang, Y. Luan, W. Dong, R. Dang, H. Gao, J. Yu, Cat. Sci.Tec, 4 (2014)
3082-3089.
[27] M. Mohammadikish, M. Masteri-Farahani, S. Mahdavi, J. Magn. Magn. Mater, 354 (2014) 317-323.
[28] T. Li, C. Yang, X. Rao, F. Xiao, J. Wang,X. Su, Ceram. Int, 41 (2015) 2214-2220.
[29] P.B. Bhat, B.R. Bhat. New. J. Chem, 39 (2015) 273-278.
[30] S. Akbarpour, A. Bezaatpour, E. Askarizadeh,M. Amiri,Appl. Organomet. Chem, 31 (2017)3804-
3813.
[31] F. Payami, A. Bezaatpour,H. Eskandari, Appl. Organomet. Chem,32 (2018) 3986-3996.
[32] B. Babaei, A. Bezaatpour, M. Amiri, S. Szunerits, R. Boukherroub, Chem. Select 3 (2018) 2877-
2881.
[33] A. Bezaatpour, F. Payami, H. Eskandari, C.R. Chim, 20 (2017) 910-920.
[34] D.M. Boghaei, A. Bezaatpour, M. Behzad, J. Coord. Chem, 60 (2007) 973-983.
[35] D.M. Boghaei, M. Behzad,A. Bezaatpour, J. Mol. Catal. A: Chem, 241 (2005) 1-7.
[36] A. Bezaatpour, S. Khatami, K. Nejati, J. Iranian. Chem. Soc, 14 (2017) 2105-2115.
[37] A. Bezaatpour, M. Behzad, V. Jahed, M. Amiri, Y. Mansoori, Z. Rajabalizadeh, S. Sarvi, React.
Kinet. Mech. Cat, 107 (2012) 367-381.
[38] R. Ghahremanzadeh, Z. Rashid, A. H. Zarnani, H. Naeimi, Appl. Catal. A: Gen, 467 (2013) 270-278.
[39] M. Bellusci, A. La Barbera, L. Seralessandri, F. Padella, A. Piozzi, F. Varsano, Polym. Int, 58 (2009)
1142-1147.
[40] C. Bianchi, F. Porta, Vacuum, 47 (1996) 179-182.

[41] J. J. Boruah, S. P. Das, S. R. Ankireddy, S. R. Gogoi,N. S. Islam, Green. Chem, 15 (2013) 2944-
2959.
[42] M. Jafarpour, A. Rezaeifard, M. Ghahramaninezhad, F. Feizpour, Green. Chem, 17 (2015) 442-452.
[43] A. Naghipour, Mater. Technol, 31 (2016) 846-853.
[44] Y. Kon, T. Yokoi, M. Yoshioka, Y. Uesaka, H. Kujira, K. Sato,T. Tatsumi, Tetrahedron. Lett, 54
(2013) 4918-4921.
[45] R. Sharma, A. Pandey, S. Gulati, Polyhedron, 45 (2012) 86-93.
[46] A. K. Sah, B. Noorullah, Catal. Lett, 145 (2015) 905-909.
Credit Author Statement
Julia A. Eremina: Investigation, Writing; Writing - Review & Editing
Abolfazl Bezaatpour: Supervision, Investigation, Writing - Review & Editing;
Hadi Basharnavaz: Writing - Review & Editing