Neodymium immobilized on Fe3O4: A new and recoverable catalyst for oxidation reactions and synthesis of 5‐substituted 1H-tetrazoles in green condition

Article abstract of DOI:10.1016/j.poly.2019.06.052

Magnetic nanoparticle functionalized with neodymium complex as catalyst and characterized by SEM, XRD, FT-IR, TGA, EDX and ICP techniques. Then, catalytic activity of prepared catalyst was examined in the synthesis of tetrezoles and oxidation reactions in

Full text of DOI:10.1016/j.poly.2019.06.052

Accepted Manuscript
Neodymium immobilized on Fe O : A new and recoverable catalyst for oxida-
3
4
tion reactions and synthesis of 5-substituted 1H–tetrazoles in green condition
Taiebeh Tamoradi, Samira Taherabadi, Mohammad Ghadermazi
PII:
S0277-5387(19)30463-2
https://doi.org/10.1016/j.poly.2019.06.052
POLY 14043
DOI:
Reference:
To appear in:
Polyhedron
Received Date:
Revised Date:
Accepted Date:
12 April 2019
12 June 2019
26 June 2019
Please cite this article as: T. Tamoradi, S. Taherabadi, M. Ghadermazi, Neodymium immobilized on Fe O : A new
3
4
and recoverable catalyst for oxidation reactions and synthesis of 5-substituted 1H–tetrazoles in green condition,
Polyhedron (2019), doi: https://doi.org/10.1016/j.poly.2019.06.052
This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers
we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and
review of the resulting proof before it is published in its final form. Please note that during the production process
errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

Neodymium immobilized on Fe O : A new and recoverable catalyst for
3
4
oxidation reactions and synthesis of 5‐substituted 1H–tetrazoles in green
condition
a,*
a
a,*
Taiebeh Tamoradi, Samira Taherabadi, Mohammad Ghadermazi,
a
University of Kurdistan, Department of Chemistry, Faculty of Science, Sanandaj, Iran
E-mail: t.tabss@yahoo.com (T.Tamoradi) and mghadermazi@yahoo.com (M.
Ghadermazi)
Abstract
Magnetic nanoparticle functionalized with neodymium complex as catalyst and
characterized by SEM, XRD, FT-IR, TGA, EDX and ICP techniques. Then, catalytic
activity of prepared catalyst was examined in the synthesis of tetrezoles and oxidation
reactions in which observed short reaction time and high yield in these reactions.
Keywords Fe O , Nd, Green, 5-substituted tetrazoles, Sulfoxides, Disulfides
3
4
Introduction
According to a green chemistry, one of the most important principles of chemistry, the
use of heterogeneous catalysts is nowadays a well-established method for control of
pollution. Thus, heterogeneous catalysts have extensively developed in organic synthesis
compared to homogenous catalysts their because of economic and industrial aspects
[1-4]. In order to preparing heterogeneous catalysts, various supports have been
proposed [5-8]. In this regard, magnetic nanoparticles are one of the important
supports due to facilitate the access of substrates to active sites, easy access to surface
in order to support functionalized, high dispersion, excellent stability (chemical and

thermal), easy synthesis and easy separation [9-18]. In the last few years,
superparamagnetic Fe O nanoparticles modified with several metal complexes such as
3
4
Ni, Cu, Pd, Co, VO, Zn, Zr, Cd, Mn and Cr in order to synthesis of heterogeneous
catalysts for organic synthesis such as oxidation reactions and synthesis of 5-
substituted tetrazoles [19-24]. On the other hand, 5-substituted tetrazoles, sulfides and
disulfides as versatile organic reagent are important and necessary component in
biological processes, chemical and pharmaceutical industry. The product of oxidation
of sulfides and thiols have received considerable importance in the development of
sensors, oil-sweetening processes and vulcanizing agents, etc [25-27]. Tetrazole
compounds have been widely used for more than one hundred because they are
nitrogen-rich heterocycles with a wide range of applications such as catalysis
technology, ligands in coordination chemistry, heterocyclic chemistry, effective
stabilizers of metallopeptide structures in organometallic chemistry, stable surrogates
for carboxylic acids [28-32].
Herein, we interest to report of the synthesis and characterization of Nd complex
supported on Fe O as a thermostable catalyst for synthesis of 5-substituted tetrazoles,
3
4
disulfides and sulfoxides in neat condition. It was also indicated that up to date, the
reports was not from Nd complex supported on Fe O in synthesis above-mentioned
3
4
compounds neat condition.
Experimental
Materials and physical measurements

All solvents and materials for performance of this project are purchased from Merck
and Sigma-Aldrich and used without further purification. The elemental analysis and
exact amount of Nd were determined by Energy-dispersive X-ray spectroscopy
(
EDAX, TSCAN) and inductively coupled plasma-optical emission spectrometry
ICP-OES), respectively. The surface morphology of nanostructures and texture
(
properties were determined by SEM using FESEM-TESCAN MIRA3 and Powder X-
ray diffraction (XRD) measurements using Co radiation source with a wave length =
1
.78897 Å, 40 kV, respectively. Melting points of all products were determined with
an Electrothermal 9100 apparatus. Thermal stability of the nanocatalyst and fourier
transform infrared (FT-IR) spectra of all samples performed by TGA measurement
Shimadzu DTG-60 instrument and a Bruker VERTEX 80 v, respectively.
Preparation of Fe O @Nd nanocatalyst
3
4
Following the method reported in the literature, we obtained Fe O nanoparticles
3
4
according to a previous report by Darabi et al [22]. Then, the modification of Fe O
3
4
was performance using the reflux of mixture contain 1 g of MNPs powder and 1.5 g of
tryptophan ligand in distilled water (30 mL) for 24 h. After the reflux of mentioned
mixture, the final prtoduct was separated by an external magnet, and washed with
ethanol/water and dried to give functionlized Fe O by tryptophan. Then, Fe O @Nd
3
4
3
4
nanocatalyst was obtained by mixing 1 g of functionlized Fe O by tryptophan and
3
4
1
.09 g Nd (NO ) .6H O in 30 mL absolute ethanol at reflux condition for 16 h.
3 3 2
General procedure for the oxidation reactions

To
mmol) was added under solvent-free condition. After the completion of reaction
monitored by TLC) in appropriate time, the separated catalyst (using by magnetic)
a
stirred
suspension
of
Fe O @Nd
in
H O
at
3
4
2
(
washed with ethyl acetate to obtained pure sulfoxide or disulfide derivatives.
General procedure for the synthesis of 5-substituted tetrazoles
To a stirred suspension of Fe O @Nd (5 mg) in H O (2 mL) at 100 °C, nitrile (1
3
4
2
mmol) and sodium azide (1.2 mmol) added to reaction mixture in appropriate time.
After the completion of reaction (monitored by TLC), the catalyst separated by
magnetic and then mixture was diluted with HCl (4 N, 10 mL). Finally, the resultant
organic layer extracted and washed with ethyl acetate to obtain corresponding
tetrazoles.
Selected spectral data
1
Methyl phenyl sulfoxide H NMR (400 MHz, CDCl , ppm): δ = 2.65 (s, 3H), 7.54–
3
H
7
.69 (m, 2H), 7.61–7.64 (m, 3H).
1
5
-(4-Nitrophenyl)-1H-tetrazole H NMR (400 MHz, DMSO, ppm): δ = 8.28–8.31
H
(m, 2H), 8.39–8.43 (m, 2H).
1
5
8
5
-(3-Nitrophenyl)-1H-tetrazole H NMR (400 MHz, DMSO, ppm): δ = 7.93 (t, J=
H
.4, 2H), 8.43–8.50 (m, 2H), 8.51–8.52 (s, 1H).
1
-(4-Chorophenyl)-1H-tetrazole H NMR (400 MHz, DMSO, ppm): δ = 7.85–8.1
H
(m, 4H).

1
1
,2-Di(naphthalen-2-yl)disulfane H NMR (400 MHz, DMSO): δ = 7.50–7.54 (m,
H
4
H), 7.66–7.77 (m, 2H), 7.92–7.96 (m, 4H), 7.98-8.03 (m, 2H), 8.05 (s, 2H) ppm.
Results and discussion
Catalyst characterization
After successful synthesis of Fe O @Nd, SEM, FT-IR, EDX, XRD, TGA, ICP and VSM
3
4
techniques were used to obtain the structure of nanocatalyst.

FeCl .4H O + FeCl .6H O
2
2
3
2
NH OH,Dionized water
4
80 °C, 30 min, N2
Fe O NP
3
4
O
H N
2
Dionized water
Reflux, 24 h
OH
HN
Nd(NO3)3
EtOH,
Reflux, 16h
The functionlized
Fe O @Nd
3
4
Fe O by tryptophan
3
4
Scheme 1. Synthesis of Fe O @Nd.
3
4
In order to successful synthesis of catalyst, FT-IR spectra of Fe O , functionlized Fe O by
3
4
3
4
-1
tryptophan and Fe O @Nd nanoparticles was recorded in the 400–4000 cm . As shown in
3
4
−
1
Fig. 1, the O-H and Fe-O stretching vibration at approximately 3400-3500 and 580 cm ,
respectively, in the FT-IR spectra of Fe O , functionlized Fe O by tryptophan and
3
4
3
4
Fe O @Nd was confirmed the presence of Fe O at all samples. In the spectrum of
3
4
3
4

functionlized Fe O by tryptophan, the characteristic absorption bands around 2850-2950
3
4
and 1620 cm-1 is correspounded of the aliphatic C-H and C=N stretching vibration,
respectively.
Fig. 1. FT-IR spectrum of Fe O (blue), functionlized Fe O by tryptophan (red),
3
4
3
4
Fe O @Nd catalyst (green).
3
4
Thermo-gravimetric analysis (TGA) of the organic groups supported on the surface
of bare Fe O nanostructure is indicated in Fig. 2. In TGA curve of catalyst, the first
3
4
step of weight loss below 100 °C corresponds to the removal of the physically and
chemically adsorbed solvents or surface hydroxyl groups, and the other weight loss
in the range of 100-600 °C (9%) corresponds to the decomposition of the organic

layers on the surface of Fe O in which verified the well grafting of organic groups
3
4
on the magnetic nanopartcles.
Fig. 2. The TGA diagram of Fe O @Nd.
3
4
SEM images of the Fe O @Nd in Fig. 3 at different magnifications were indicated
3
4
that the mentioned nanocatalyst was made up of uniform spherical particles with
size approximately 34 nm. It should be noted that the obtained morphology assisted
to maximize the simultaneous increasing of the catalyst efficiency and frequency of
molecular interactions or decreasing activation energy of rate determining step.

Fig. 3. SEM images of Fe O @Nd catalyst at 1μ (a), 500 nm (b) and 200 nm (c)
3
4
magnifications.
The energy-dispersive X-ray spectroscopy (EDX) analysis of Fe O @Nd nanocatalyst was
3
4
confirmed the presence of Fe, O, N, C and Nd specie in the obtained catalyst (Fig. 4), and
-1
amount of Nd loaded on modified magnetic nanoparticles was obtained 0.22 mmol g .

Fig. 4. EDX spectrum of Fe O @Nd.
3
4
The structural and textural properties of the Fe O @Nd nanocatalyst was determined by
3
4
powder X-ray diffraction. As seen in Fig.5, the presence of a six peaks assigned to (2 2 0), (3
1), (4 0 0), (4 2 2), (5 1 1), and (4 4 0) reflections was verified the magnetite phase
JCPDS#01-075-0449) of Fe O which crystallized in the cubic system. Also, the XRD
1
(
3
4
pattern of prepared nanocatalyst indicated that the Fe O phase has not been changed during
3
4
the modifications [22].

Fig.5. XRD pattern of Fe O @Nd.
3
4
Catalytic studies
Also, we tested catalytic activity of Fe O @Nd in the oxidation reactions (Scheme 2 and 3)
3
4
and 5-substituted tetrazoles (Scheme 4). After the design of various experiments in order to
optimize of the reaction conditions such as solvent, amount of catalyst and H O , the best
2
2
results were obsvered in the presence of 5 mg Fe O @Nd and 0.5 mL H O under solvent
3
4
2
2
free (Table 1).
O
S
Fe O @Nd
3
4
S
R1
R2
Solvent-Free, H O , RT
R1
R2
2
2
1a-1i
2a-2i
Scheme 2. Fe O @Nd catalyzed the oxidation of sulfides to sulfoxide.
3
4

Table 1. Optimization of oxidation of sulfides to the corresponding
sulfoxides using Fe O @Nd nanoparticles under various conditions
3
4
.
Entry
Solvent
H O
Catalyst
Time
(min)
45
10
10
15
55
60
80
Yield (%)a
2
2
(mg)
1
2
3
4
5
6
7
Solvent-Free
Solvent-Free
Solvent-Free
Solvent-Free
Ethanol
0.5
0.5
0.5
0.4
0.5
0.5
0.5
3
5
7
7
7
7
7
65
96
99
92
81
60
55
Ethyl acetate
Acetonitrile
aIsolated yields.
Then, Fe O @Nd catalytic activity investigated in the wide range of sulfides with different
3
4
functional groups in which observed results good to excellent (Table 2).
More importantly, because of mild conditions of described heterogeneous systems, there is no
overoxidation to sulfone for oxidation of sulfides.
O
O
O
Catalyst
H O
S
S
S
+
R1
R2
2
2
R1
R2
R1
R2
100%
0%
Scheme 3. Oxidation of sulfides to the corresponding sulfoxides.
Table 2. Oxidation of sulfides to the sulfoxides in the presence of Fe O @Nd.
3
4
Entry
Substrate
Product Time Yield
min) (%)a
TON
TOF
M.p.
(°C)
(
-1
(
h )
1
2
3
Dipropylsulfide
Diethylsulfide
Dibenzylsulfide
2a
2b
2c
22
25
17
94
95
88
854
864
800
2308
2057
2857
Oil [11]
Oil [11]
127 [19]

4
Benzylphenylsulfide 2d
Tetrahydrothiophene 2e
35
95
864
1490
117-120
11]
10181 Oil [21]
[
5
6
7
8
5
93
92
94
88
845
836
854
800
Ethylphenylsulfide
Diphenylsulfide
2f
12
25
20
4180
2033
2424
Oil [21]
61 [21]
206-208
[21]
2g
3,3′-Thiodipropionic 2h
acid
9
Methylphenylsulfide 2i
10
96
873
5456
Oil [21]
a
Isolated yields
Also, the synthesis of disulfide derivatives was investigated in the presence of
Fe O @Nd catalyst (Scheme 4). Initially, condition of oxidation of 4-
3
4
methylthiophenol was optimized that the best results were obtained in the presence
of 5 mg of catalyst and 0.4 mL H O under solvent free (Table 3). Melting points of
2
2
the obtained products in Table 3 were 40-44 °C.
R3
Fe O @Nd
3
4
3
S
S
R SH
R3
Solvent-Free, H O , R.T
2
2
2
a-2g
1a-1g
Scheme 4. Fe O @Nd catalyzed the oxidation of thiols to disulfides.
3
4
Table 3. Optimization of oxidative coupling of thiols into disulfides
using Fe O @Nd under various conditions.
3
4
Entry
Solvent
H O
Catalyst
mg)
Time
(min)
40
Yield (%)a
2
2
(
1
2
3
4
5
Solvent-Free
Solvent-Free
Solvent-Free
Solvent-Free
EtOH
0.5
0.5
0.5
0.4
0.5
3
7
5
5
5
55
98
94
94
80
17
20
22
50

6
7
Ethyl acetate
Acetonitrile
0.5
0.5
5
5
85
80
88
81
aIsolated yields.
Then, in order to expand our study on synthesis of disulfides, a wide range of thiols was
oxidated under the optimized condition in which indicated that products obtained in short
time and good to excellent yiels (Table 4).
Table 4. Oxidative coupling of thiols into disulfides using H O in the presence of Fe O @Nd.
2
2
3
4
Entry Substrate
Product
Time
Yield
(%)a
94
TON
TOF
M.p. (°C)
-1
(min)
(h )
1
2
3
4-Methylbenzenethiol
4a
4b
4c
22
854
854
836
2308
2588
629
41-43 [21]
133 [11]
273 [11]
Naphthalene-2-thiol
2-Mercaptobenzoic
acid
20
94
80
92
4
Benzo[d]thiazole-2-
thiol
4d
40
96
873
1323
173-176
[21]
5
6
2-Mercaptoethanol
Benzo[d]oxazole-2-
thiol
4e
4f
35
35
88
97
800
882
1379
1521
Oil [21]
92 [11]
7
Benzyl mercaptan
4g
25
98
891
2121
57 [21]
a
Isolated yields
Finally, the synthesis of 5-(3-nitrophenyl)-1H-tetrazole was investigated in the different
conditions such as solvent, temperature and amount of catalyst (Scheme 5) in which observed

that the best results were obtained with 4 mg of Fe O @Nd and H O as green solvent 80 °C
3
4
2
(Table 5).
CN
N
HN
N
Fe O @Nd
3
4
N
o
NaN , H O, 80 C
3
2
R
R
6a-6h
5a-5h
Scheme 5. Fe O @Nd catalyzed the one-pot synthesis of 5-substituted tetrazoles.
3
4
Table 5 Optimization of reaction conditions for synthesis of 5-(3-nitrophenyl)-1H-
tetrazole in the presence of Fe O @Nd.
3
4
o
Yield (%)a
Entry
1
Solvent
Temp ( C)
Catalyst
Time
(min)
15
(mg)
PEG
EtOH
DMSO
80
80
80
80
80
80
80
60
100
6
90
92
90
92
95
92
75
80
94
6
25
2
6
20
4
H O
2
6
15
5
H O
2
8
10
6
H O
2
4
8
7
H O
2
2
35
8
H O
2
4
20
9
H O
2
4
8
aIsolated yields.
After optimization of reaction condition, a scope of the reaction, a series of aromatic
tetrazoles was synthesized at same condition and results of this study were summarized in
Table 6.

Table 6 Synthesis of 5-substituted 1H-tetrazole derivatives in the presence of Fe O @Nd
3
4
under optimized reaction conditions.
Entry Substrate
Product Time Yield
min) (%)a
TON
1000
1022
TOF
M.p. (°C)
202-205
-1
(
(h )
1
3
Phthalonitrile
4a
25
90
2380
7861
1152
[
21]
156-158
11]
182 [11]
3-Nitrobenzonitrile
4b
8
92
[
4
5
6
2-Chlorobenzonitrile
2-Hydroxybenzonitrile
4-Hydroxybenzonitrile
4c
4d
4e
55
30
15
95
91
94
1055
1011
1044
2022 221-223[11]
4176
236-238
21]
[
7
8
9
4-Chorobenzonitrile
4-Nitrobenzonitrile
Benzonitrile
4f
4g
4h
55
10
80
88
97
88
978
1078
978
1068
6737
257 [21]
223 [11]
735 21-212 [21]
aIsolated yields.
Consideration the reusability of catalyst is a one of important factors in dustry, the reusability
of the oxidation of methyl phenyl sulfide, coupling of 4-methylthiophenol and 5-(4-
nitrophenyl)-1H-tetrazole was investigated. (Fig. 6).

Fig. 6. Reusability of Fe O @Nd in the oxidation of methyl phenyl sulfide (a), coupling of 4-
3
4
methylthiophenol (b) and 5-(4-nitrophenyl)-1H-tetrazole (c).
The nature of the recovered catalyst was investigated by EDX (Fig. 7) and FT-IR
(Fig. 8) analysis. It was be observed that the catalyst can be recycled without any
significant change in its structure.
Fig. 7. EDX spectrum of recovered Fe O @Nd catalyst.
3
4
Fig. 8. FT-IR spectrum of recovered Fe O @Nd catalyst.
3
4

Comparison of the catalyst
Also, the obtained results of the oxidation of methylphenyl sulfide in this methodology were
shown ease of operation, short reaction time, commercially available materials and high yield
in the compare with previously reported methods (Table 7).
3 4
Table 7. Comparison of Fe O @Nd for the oxidation of methylphenyl sulfide with previously reported
procedure.
Entry
Substrate
Catalyst
Time (min)
Yield (%)a
72 [33]
1
2
3
Methylphenylsulfide
Methylphenylsulfide
Methylphenylsulfide
Silica sulfuric acid/H
2
O
2
60
55
45
Fe
Cu(II)–Schiff base
complex- Fe /H
VO-2A3HP-MCM-41
2NaBO .4H O(I)/KBr
Zr-oxide@MCM-41
VO 2F(dmpz)
3
O
4
-Adenine-Ni
98 [34]
90 [35]
3
O
4
2 2
O
4
5
6
7
8
9
Methylphenylsulfide
Methylphenylsulfide
Methylphenylsulfide
Methylphenylsulfide
Methylphenylsulfide
Methylphenylsulfide
Methylphenylsulfide
120
120
300
300
10
96 [36]
57 [37]
3
2
98 [38]
2
95 [39]
Fe
3
O
4
Trace
Fe
3
O
4
@Tryptophan
10
Trace
1
0
Fe @Nd
3
O
4
10
96 [this work]
aIsolated yields.
Conclusion
In summary, in order to synthesis of Nd magnetic catalyst, Nd complex was successfull
immobilized on Fe O . Then this nanocatalyst characterized by versatile chemical and
3
4

physical techniques such as SEM, XRD, FT-IR, TGA, EDX and ICP and its catalytic
behavier studied in the synthesis of 5-substituted tetrazoles and the oxidation reactions in
green condition in which observed outstanding properties from present procedure such as
ease of separation via magnetic field, high yield, the use of Nd as a new active site in organic
reaction, high reusability of the catalyst.
Acknowledgements
We gratefully acknowledge the support of this work by University of Kurdistan.
References
1
.
A, Michrowska, L. Gułajski, Z. Kaczmarska, K. Mennecke, A. Kirschningd, K. Grela,
Green Chem. 8 (2006) 685.
2
5
3
4
8
5
6
7
3
8
9
.
T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, New. J. Chem 42 (2018)
479.
. Rafiee E, Eavani S, Green Chem 13 (2011) 2116.
.
T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Catal Lett 148 (2018)
57.
.
.
.
J. Davarpanah, A.R. Kiasa, Catal Commun 46 (2014) 75.
M. A. Zolfigol, M. Yarie, Appl. Organometal. Chem 31 (2017) e3598.
T. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, Appl. Organometal. Chem
2 (2018) e4340.
. W.Y. Hao, j.c. Sha, S.R. Sheng, M.Z. Cai, Catal. Commun 10 (2008) 257.
.
D. Saberi, M. Sheykhan, K. Niknam, A. Heydari, Catal. Sci. Technol, 3 (2013) 2025.

1
1
0. A. Maleki, P. Ravaghi, M. Aghaei, H. Movahed, Res. Chem. Intermed 43 (2017)
485.
5
1. A. Maleki, J. Rahimi, O.M. Demchuk, A.Z. Wilczewska, R. Jasiński, Ultrason.
Sonochem. 43 (2018) 262.
1
1
1
2. A. Maleki, Polycycl. Aromat. Compd. 38 (2018) 402.
3. A Maleki, R Rahimi, S Maleki, Environ. Chem. Lett. 14 (2016,) 195.
4. Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset JM, Chem. Rev. 111
(
2011) 3036.
5. T. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, New. J. Chem 41 (2017)
1714.
6. M.A. Zolfigol, M. Kiafar, M. Yarie, A. Taherpour, M. Saeidi-Rad, RSC Adv 6
2016) 50100.
7. A. Maleki, J. Rahimi, Z. Hajizadeh, M. Niksefat, J. Organomet. Chem. 881 (2019)
8.
1
1
1
1
(
5
1
1
8. A Maleki, M Niksefat, J Rahimi, S Azadegan, Polyhedron. 167 (2019) 103.
9. M.A. Zolfigol, V. Khakyzadeh V, A.R. Moosavi-Zare, A. Rostami, A. Zare, N.
Iranpoor, M.H. Beyzavi, R. Luque, Green Chem 15 (2013) 2132.
2
2
2
2
0. T. Tamoradi, B. Mehraban-Esfandiari, M. Ghadermazi, A. Ghorbani–Choghamarani,
Res Chem Intermed 44 (2018) 1363.
1. A. Ghorbani-Choghamarani, Z. Darvishnejad, B. Tahmasbi, Inorg. Chim. Acta 435
(2015) 223.
2. M. Darabi, T. Tamoradi, M. ghadermazi, A. Ghorbani-Choghamaran,, Trans Metal
Chem 42 (2017) 703.
3. A. Ghorbani-Choghamarani, B. Tahmasbi, P. Moradi, Appl Organometal Chem 30
(2016) 422.

2
2
4. T. Tamoradi, A. Ghorbani-Choghamarani, M. Ghadermazi, Polyhedron 145 (2018)
20.
5. M. Azizi, A. Maleki, F. Hakimpoor, R. Ghalavand, A. Garavand, Catal. Lett. 147
2017) 2173.
1
(
2
2
2
2
3
6. H. Veisi, S. Sajjadifar, P.M. Biabri, S Hemmati, Polyhedron, 153 (2018) 240.
7. A. Maleki, A. Sarvary, RSC Adv. 5 (2015) 60938.
8. M. Bagherzadeh, M. Zare, Adv Heretocyclic Chem 123 (2017) 1.
9. U.B. Patil, K.R. Kumthekar, J.M. Nagarkar, Tetrahedron. Lett 53 (2012) 3706.
0. M. Esmaeilpour, J. Javidi, F. Nowroozi Dodeji, M. Mokhtari Abarghoui, J Mol Catal
A 393 (2014) 18.
3
3
3
1. F. Abrishami, M. Ebrahimikia, F. Rafiee, Appl Organometal Chem 29 (2015) 730.
2. A Sarvary, A Maleki, Mol. Divers. 19 (2015) 189.
3. A. Shaabani, A.H. Rezayan, Silica sulfuric acid promoted selective oxidation of
sulfides to sulfoxides or sulfones in the presence of aqueous H O , Catal. Commun. 8
2
2
(2007) 1112.
3
3
3
4. T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Ghorbani-Choghamarani
A, Appl. Organometal. Chem 32 (2018) e3974.
5. A. Ghorbani-Choghamarani, Z. Darvishnejad, M. Appl. Organomet. Chem. 29
(2015) 170.
6. M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, Appl. Organometal.
Chem 30 (2016) 236.
3
3
3
7. A. Dhakshinamoorthy, K. Pitchumani, Catal Commun 10 (2009) 872.
8. M. Hajjami, L. Shiri, A. Jahanbakhshi, Appl. Organometal. Chem 29 (2015) 668.
9. S. Hussain, D. Talukdar, S.K. Bharadwaj, M.K. Chaudhuri, Tetrahedron Lett. 53
(2012) 6512.

Graphical Abstract
Neodymium immobilized on Fe O as recoverable catalyst
3
4
a,*
a
a,*
Taiebeh Tamoradi, Samira Taherabadi, Mohammad Ghadermazi,
a
University of Kurdistan, Department of Chemistry, Faculty of Science, Sanandaj, Iran
E-mail: t.tabss@yahoo.com (T.Tamoradi) and mghadermazi@yahoo.com (M.
Ghadermazi)

Graphical Abstract - Synopsis
The present work, we prepared a novel catalyst by linking Nd complex on Fe O
3
4
nanoparticles as green catalyst and characterized by FT-IR, SEM, EDX, ICP-OES, XRD and
TGA methods. Then, catalytic activity of this catalyst was tested in the oxidation reactions
and synthesis of tetrazoles. Easy preparation and easy separation, chemical and hydrothermal
stability, the use of inexpensive materials, high reusable are outstanding properties of this
protocol.