Immobilization of copper nanoparticles on WO3 with enhanced catalytic activity for the synthesis of 1,2,3-triazoles

Article abstract of DOI:10.1002/aoc.5959

In this study, a heterogeneous catalyst based on copper nanoparticles immobilized on metal oxide, WO₃, was fabricated using an impregnation method as an easy and straightforward nanoparticle synthesis strategy. The successful synthesis of the n

Full text of DOI:10.1002/aoc.5959

Received: 24 March 2020
DOI: 10.1002/aoc.5959
Revised: 18 June 2020
Accepted: 1 July 2020
F U L L P A P E R
Immobilization of copper nanoparticles on WO3 with
enhanced catalytic activity for the synthesis of
1,2,3-triazoles
Mojtaba Amini1
| Elham Hajipour1 | Ali Akbari2
| Keun Hwa Chae3
1Department of Chemistry, Faculty of
Science, University of Maragheh,
Maragheh, Iran
2Solid Tumor Research Center, Cellular
and Molecular Medicine Institute, Urmia
University of Medical Sciences,
Urmia, Iran
3Advanced Analysis Center, Korea
Institute of Science and Technology,
Seoul, 136-791, South Korea
In this study, a heterogeneous catalyst based on copper nanoparticles
immobilized on metal oxide, WO3, was fabricated using an impregnation
method as an easy and straightforward nanoparticle synthesis strategy. The
successful synthesis of the nanocatalyst was confirmed using various spectro-
scopic techniques such as X-ray diffraction, scanning electron microscopy,
energy dispersive X-ray analysis, and transmission electron microscopy. The
catalytic performance of the well-characterized material was evaluated
through the azide–alkyne cycloaddition reaction (click reaction) in the aque-
ous medium. To optimize reaction conditions, different reaction parameters
such as nanocatalyst amount, reaction time, temperature, and solvents were
studied. Experimental results showed that as-prepared nanocatalyst (Cu/WO3)
could act as an effective and reusable heterogeneous catalyst in water for the
synthesis of 1,2,3-triazoles in good-to-excellent yields. In addition, Cu/WO3
has some advantages such as simple preparation procedure, easy separation,
and recyclability for three runs with no remarkable loss of catalytic activity,
which is essential from a catalytic application point of view.
Correspondence
Mojtaba Amini, Department of
Chemistry, Faculty of Science, University
of Maragheh, Maragheh, Iran.
Email: mamini@maragheh.ac.ir
Ali Akbari, Solid Tumor Research Center,
Cellular and Molecular Medicine
Institute, Urmia University of Medical
Sciences, Urmia, Iran.
Email: akbari.a@umsu.ac.ir
K E Y W O R D S
catalytic activity, click reaction, copper, nanoparticles, WO3
1 | INTRODUCTION
alkynes.[6] In 2002, Sharpless et al.[7] successfully synthe-
sized these compounds in the presence of catalytic
Rational design and synthesis of structurally complex
heterocyclic molecules have attracted much attention
from synthetic organic and medicinal chemists.[1] Among
them, triazoles,[2] especially, N-substituted 1,2,3-triazoles,
as substantial intermediates have more potential utiliza-
tion in the synthesis of some important drugs with
unique biological and pharmaceutical properties such as
antiviral, antitubercular,[3] antidiabetic, anticancer,[4]
selective β3 adrenergic receptor agonist, and anti-HIV
activities.[5] Traditionally, the synthesis of 1,2,3-triazoles
was carried out in harsh reaction conditions and often
led to the two regioisomers by using asymmetric
amounts of Cu(I) at ambient temperature with high
regioselectivity in a short time. In general, organic reac-
tions in homogenous media have some disadvantages,
such as low catalytic performance, difficulty in product
purification, and catalyst recyclability.[8] Using heteroge-
neous versions of catalysts could be considered as an
effective approach to reduce these limitations.[9] How-
ever, despite various useful advantages of heterogeneous
catalysts, their low activity and aggregation tendency are
reported to be challenging.[10] The solution to these prob-
lems is the immobilization of various types of metal
nanoparticles (NPs) on different heterogeneous
Appl Organomet Chem. 2020;e5959.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5959

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AMINI ET AL.
supports.[11] For example, a broad range of polymeric
materials have been used as active solid supports for cop-
per NPs (Cu NPs) in the click synthesis of 1,2,3-triazoles
between azides and alkynes.[12] In addition, massive
research interests have been devoted to transition metal
oxide materials owing to their exceptional physicochemi-
cal properties, and over the past two decades, they have
been employed extensively as solid supports for various
metal NPs.[13] Among all existing transition metal oxides,
WO3—with its excellent physical properties such as pie-
zoelectricity, electrical conductivity, and defect
structures—has gained prominence as one of the useful
supports for metal NPs.[14] For instance, prepared
Cu/WO3 materials have wide applications in gas sensors
and solid-state drives.[15] From a catalytic application
point of view, no reports on various organic reactions in
the presence of Cu/WO3 have been reported.[13] Further
to our research on the synthesis and applications of vari-
ous nanomaterials,[16] in this study, WO3 was synthesized
by the impregnation method followed by immobilization
of copper nanoparticles (Cu NPs) to prepare Cu/WO3
nanomaterials, and then, for the first time, the catalytic
activity of the synthesized Cu/WO3 was evaluated in the
click reaction.
a 25-ml round-bottom flask containing 10 ml H2O, a cer-
tain amount of Na2WO4Á2H2O (0.825 g, 2.5 mmol) was
added and acidified with a 6 M HCl solution. The precipi-
tated white solid WO3ÁnH2O was washed thrice with
water and dried at 50ꢀC. Finally, to prepare WO3
nanoparticles, the solid WO3ÁnH2O was dehydrated at
500ꢀC. An impregnation strategy was used to immobilize
Cu NPs (Cu/WO3) in the presence of Cu(NO3)2Á3H2O as
a source of Cu. In short, in a 50-ml round-bottom flask
containing 20 ml methanol, WO3 (0.1 g) and
Cu(NO3)2Á3H2O (0.2 g) were added and stirred vigorously
for 24 h. After impregnation, Cu NPs were synthesized by
a reduction of the Cu/WO3 with 0.5 ml hydrazine
hydrate. The final sample was filtered, washed with
methanol, and dried at room temperature.
2.3 | General procedure for Cu/WO3 base
azide–alkyne cycloaddition
A round-bottom flask containing 2 ml H2O was charged
with Cu/WO3 along with a certain amount of alkyne
(0.5 mmol), organic halide (0.55 mmol), and NaN3
(0.55 mmol). The reaction mixture was stirred at 90ꢀC for
12 h. The total conversion of starting materials was moni-
tored using thin-layer chromatography. Filtration was
used for catalyst recovery, and the desired products were
extracted with EtOAc (2 × 10 ml) without any additional
purification steps.
2 | EXPERIMENTAL
2.1 | Materials and characterization
instruments
Hydrochloric acid (HCl, 37%), Na2WO4Á2H2O, Cu(NO3)2,
sodium azide, hydrazine hydrate, all alkynes (phenyl
acetylene and propargyl alcohol), all organic halides
(benzyl chloride, benzyl bromide, 2-nitrobenzyl chloride,
4-nitrobenzyl chloride, and 2-methylbenzyl chloride),
and solvents were provided by Fluka and Merck
(Germany) and utilized with no extra purification. Trans-
mission electron microscopy (TEM, FEI Tecnai 20) was
used to determine the structure, shape, and size of the
sample. Scanning electron microscopy (SEM) analysis
was carried out with Philips CM120 and LEO 1430VP
instruments with an energy dispersive X-ray (EDX) spec-
troscopy. The X-ray powder profiles were recorded using
a Bruker D8 ADVANCE (Germany) diffractometer (Cu-
Kα radiation).
3 | RESULTS AND DISCUSSION
3.1 | Characterization of the catalyst
(Cu/WO3)
The structure and phase formation of the samples were
determined using X-ray diffraction (XRD) profiles of
WO3 support and Cu/WO3 nanocatalyst. As shown in
Figure 1, all WO3 support peaks related to lattice reflec-
tion planes are in a good agreement with JC-PDS
01–075-2072.[18] Because a low amount of copper was
immobilized on the support, there were no differences
between the XRD profiles of WO3 and Cu/WO3. On the
contrary, copper atoms occupied the lattice position of
WO3, resulting in the absence of copper peaks in the pat-
tern of Cu/WO3.[17]
The morphology and elemental composition of the
synthesized Cu/WO3 were studied using SEM and EDX
analyses, respectively. Figure 2a,b shows the SEM images
of Cu/WO3 with two different magnifications. Spherical-
shaped aggregated nanoparticles could be seen easily in
Figure 2b. The EDX data are shown in Figure 2c, which
2.2 | Preparation of WO3 and immobilized
copper nanoparticles (Cu/WO3)
The synthesis of WO3 nanoparticles was carried out fol-
lowing our previously reported procedure.[17] In short, in

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Immobilized Cu NPs with a size of about 2–5 nm on
WO3 support were observed in TEM image (Figure 3).
3.2 | Catalytic experiments
The catalytic activity of the synthesized Cu/WO3 catalyst
was evaluated in the 1,3-dipolar azide–alkyne cycloaddi-
tion reaction. For this, the reaction between
phenylacetylene and benzyl chloride in the presence of
sodium azide was selected as a model reaction.[12b] To
optimize the reaction parameters, the model reaction was
subjected to various reaction conditions as summarized
in Table 1.
Entries 1–5 show the effect of catalyst amount on the
yield of model reaction. In the absence of a catalyst
(entry 1), there was no progress in the reaction, which
demonstrated the need for the Cu/WO3 catalyst to
obtain the desired product. The product yield increased
from 66 to 82% at 90ꢀC when the amount of catalyst was
increased from 1 to 5 mg. When the reaction tempera-
ture increased from room temperature to 90ꢀC, there
was a remarkable increase in the product yield (entries
5–8). As shown in entry 4 of Table 1, the product,
1-benzyl-4-phenyl-1,2,3-triazole, has the highest yield
(82%) at 90ꢀC after 12 h. Based on this result, 90ꢀC was
selected as the optimum reaction temperature in all the
remaining experiments. Furthermore, the time depen-
dency of the click reaction was evaluated and is pres-
ented in Table 1. By running the reaction in less than
12 h, the amount of the isolated desired product was low
FIGURE 1 X-ray diffraction profiles of WO3 and Cu/WO3
nanoparticles
confirms the presence of Cu and W elements in the struc-
ture of Cu/WO3 catalyst. The content of Cu and W was
12.78 and 76.03 wt%, respectively.
FIGURE 2 (a,b) Scanning electron
microscopy images of the Cu/WO3
catalyst with two different
magnifications and (c) energy dispersive
X-ray analysis of Cu/WO3

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AMINI ET AL.
(entry 12), but in the case of water as a green solvent (entry
4), 82% product yield was achieved. The reason is that
sodium azide salt is completely soluble in water, leading to
the rapid synthesis of reaction intermediates. Finally,
entry 4 was selected as the best optimized condition in
which the model click reaction was conducted in the pres-
ence of 5 mg Cu/WO3 catalyst in water at 90ꢀC for 12 h.
With this optimized condition, the scope of the general
applicability of Cu/WO3 catalyst was evaluated toward the
reaction of different alkynes and substituted benzyl
halides. Experimental results are summarized in Table 2.
As could be seen, substitution variations on the phenyl
ring of benzyl halides were investigated, and all of them
yielded the desired products in good-to-excellent yields
(entries 1–5). Due to steric hindrance, the ortho substitute
of the nitro group on benzyl chloride led to a low product
yield compared to its para substitute (entries 3 and 5). In
addition, the product yield of aliphatic alkyne was less
than that of phenylacetylene in all experiments (entry 6).
In general, the formation of 1,2,3-tetrazole via the
click reaction proceeded smoothly to obtain the
corresponding 1,4-disubstituted-1,2,3-triazole derivatives.
A tentative stepwise mechanism (Figure 4) similar to
those of other Cu(I)-catalyzed azide–alkyne cycloaddition
reactions was proposed, involving the generation of the
FIGURE 3 Transmission electron microscopy image of the
Cu/WO3 catalyst
(entries 8 and 9). The effect of various solvents on the
catalytic activity of Cu/WO3 was also investigated. In
general, solvents as a reaction medium play an important
role in increasing the solubility of the starting materials.
As shown in Table 1 (entries 9–13), when the click
reaction was catalyzed by Cu/WO3, an increase in the
reaction conversion was observed in the order of
H2O > CH3CN > acetone > C2H5OH > toluene. On the
contrary, there was no progress in reaction in toluene
TABLE 1 Results of the azide–alkyne cycloaddition reaction at different reaction conditions
Entry
Catalyst amount (mg)
Solvent
H2O
T (ꢀC)
90
Time (h)
Yield (%)a
1
0
1
3
5
5
5
5
5
5
5
5
5
5
12
12
12
12
12
12
12
4
0
2
H2O
90
66
71
82
0
3
H2O
90
4
H2O
90
5
H2O
r.t
6
H2O
40
48
67
55
72
48
65
N.R.b
57
7
H2O
70
8
H2O
90
9
H2O
90
8
10
11
12
13
C2H5OH
CH3CN
Toluene
Acetone
90
12
12
12
12
90
90
90
aIsolated yield.
bNo reaction.

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TABLE 2 Click reaction of different starting materials in the presence of Cu/WO3 catalyst
Entry
Benzyl halide
Alkyne
Product
Yield (%)
Melting point (ꢀC)ref
1
82
125–126 (126–127)[19]
125–126 (126–127)[20]
145–147
2
3
91
84
4
5
6
70
95
35
106–107 (105–106)[21]
156–157 (156–157)[22]
78–79 (78–78.5)[19]
copper(I) acetylide via the insertion of Cu(I) into termi-
nal alkynes followed by the addition of the alkyl–azide
intermediate.
To evaluate the reusability of the catalyst, a set of
reactions between benzyl chloride, NaN3, and
phenylacetylene were conducted with water as a solvent.
At the end of the first run, the used catalyst was removed
from the reaction mixture by centrifugation, washed, and
dried at 40ꢀC to use for the next run. As shown in
Figure 5, the catalyst could be recycled at least thrice
without significant yield loss.
To date, many different catalysts with several disad-
vantages are being used for the synthesis of 1,2,3-triazole
derivatives. Table 3 summarizes a comparison of the
results obtained for the as-prepared Cu/WO3 catalytic
system with those reported in the literature. Cu(II)–PBS–
HPMO and SiO2–NHC-Cu(I) catalysts (Table 3, entries
1 and 2) were prepared through multistep processes for a

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AMINI ET AL.
long time. In the presence of Cu/Al2O3, the reaction was
carried out under severe conditions such as ball milling
(Table 3, entry 3). PS–C22–CuI and Cu(I)–zeolite cata-
lysts led to the formation of the desired product at a low
temperature, but the reaction took a long time (Table 3,
entries 4 and 5). Moreover, the fabrication of Cu@βCD–
PEG–mesoGO and CuNPs/Mag silica are so hard and
expensive (Table 3, entries 6 and 7). In summary,
according to Table 3, each reported protocol has its own
merits as well as demerits. However, from the point of
cost, easy and straightforward catalyst preparation, oper-
ational simplicity, and relatively low reaction time, the
Cu/WO3 catalyst synthesized in this study is superior and
easily adaptable.
To evaluate the heterogeneity of the synthesized cata-
lyst, a leaching experiment was carried out. In this
regard, after the reaction was run for 4 h, the catalyst
was separated by centrifugation and then the reaction
was continued for 12 h. It was found that no product was
obtained, suggesting the high stability of catalyst during
the reaction process. Moreover, inductively coupled
plasma (ICP) analysis was used to measure the copper
content in the recycled Cu/WO3 catalyst, which showed
that the copper contents of the fresh catalyst and the
second-run reused catalyst were 12.3 and 16.0 w/w%,
respectively. This result indicated that very low leaching
amount of copper occurred in the reaction mixture.
FIGURE 4 Tentative mechanism of azide–alkyne
cycloaddition reaction
4 | CONCLUSIONS
The Cu NPs immobilized on WO3 support were fabri-
cated and characterized using XRD, SEM–EDX, and
TEM. The synthesized novel material was found to be
an effective catalyst in the click reaction of alkynes
with various benzyl halides in the presence of sodium
azide. This reaction could be considered an important
FIGURE 5 Reusability evaluations of the Cu/WO3 catalyst in
the azide–alkyne cycloaddition reaction
TABLE 3 Comparison of Cu/WO3 heterogeneous catalyst toward click reaction with other reported catalysts
Entry
Catalyst
Reaction condition
100ꢀC, H2O
80ꢀC, H2O
Time (h)
Yield (%)
Ref.
[23]
1
2
3
4
5
6
7
8
Cu(II)–PBSa–HPMO
SiO2–NHC–Cu(I)
Cu/Al2O3
3.5
6
96
98
92
99
80
90
98
82
[24]
[25]
[26]
[27]
[28]
[29]
Ball milling, Rt
1
PS–C22–CuIb
Rt, H2O
15
15
1
Cu(I)–zeolite
20ꢀC, MeOH
25ꢀC, H2O
Cu@βCD–PEG–mesoGOc
CuNPs/Mag silica
Cu/WO3
70ꢀC, H2O
1
90ꢀC, H2O
12
This work
aPorphyrin-bridged silsesquioxane.
bPolystyrene resin-supported copper(I) iodide–cryptand-22 complex.
cCopper-supported β-cyclodextrin-functionalized PEGylated mesoporous silica nanoparticle–graphene oxide hybrid.

AMINI ET AL.
7 of 8
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are very substantial intermediates in organic and
medicinal chemistry. To optimize the reaction condi-
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ACKNOWLEDGMENTS
The authors thank the University of Maragheh for finan-
cial support of this work.
[10] N. Moeini, T. Tamoradi, M. Ghadermazi, A. Ghorbani-
Choghamarani, Appl. Organomet. Chem. 2018, 32, e4445.
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AUTHOR CONTRIBUTIONS
Mojtaba Amini: Supervision. Elham Hajipour: Con-
ceptualization; methodology. Keun Hwa Chae: Software.
AUTHOR CONTRIBUTION
Mojtaba Amini supervised the study, Elham Hajipour
conceptualized the study and devised methodology, Ali
Akbari wrote the original draft, and Keun Hwa Chae
used software to generate data.
[12] a) M. Ghavidel, S. Y. Shirazi Beheshtiha, M. Heravi, Int.
J. Nano Dimen. 2018, 9, 408. b) A. Akbari, A. Naderahmadian,
B. Eftekhari-Sis, Polyhedron 2019, 171, 228. c)
G. R. Mahdavinia, M. Soleymani, M. Nikkhoo, S. M. F. Farnia,
M. Amini, New J. Chem. 2017, 41, 3821.
FUNDING INFORMATION
The authors thank the University of Maragheh for finan-
cial support of this work.
[13] A. Akbari, M. Amini, A. Tarassoli, B. Eftekhari-Sis,
N. Ghasemian, E. Jabbari, Nano-Struct. Nano-Obj. 2018,
14, 19.
[14] N. Prabhu, S. Agilan, N. Muthukumarasamy, T. Senthil, Int.
J. Chem. Technol. Res. 2014, 6, 3487.
ORCID
Mojtaba Amini https://orcid.org/0000-0001-6509-5942
Ali Akbari https://orcid.org/0000-0001-6027-292X
[15] Y. Yao, K. Yamauchi, G. Yamauchi, T. Ochiai, T. Murakami,
Y. Kubota, J. Biomater. Nanobiotech. 2012, 3, 421.
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How to cite this article: Amini M, Hajipour E,
Akbari A, Hwa Chae K. Immobilization of copper
nanoparticles on WO3 with enhanced catalytic
activity for the synthesis of 1,2,3-triazoles. Appl
Organomet Chem. 2020;e5959. https://doi.org/10.
1002/aoc.5959
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