Zirconium oxide complex anchored on boehmite nanoparticles as highly reusable organometallic catalyst for C–S and C–O coupling reactions

Article abstract of DOI:10.1002/aoc.4396

Boehmite nanoparticles were prepared by a simple and inexpensive procedure in water using commercially available materials without inert atmosphere. Then, the surface of the boehmite nanoparticles was modified using 3-mercaptopropyltrimethoxysilane and subsequently zirconium oxide was supported on the modified surface. Zirconium oxide supported on boehmite nanoparticles (Pr.S-ZrO@boehmite) was characterized using scanning electron microscopy, Fourier transform infrared spectroscopy, thermogravimetric analysis and inductively coupled plasma technique. The catalytic application of Pr.S-ZrO@boehmite was studied in C–O and C–S coupling reactions for synthesis of valuable compounds such as ether and sulfide derivatives. All products were obtained in good to excellent yields and the catalyst could be recovered and reused several times without significant loss of catalytic efficiency. Furthermore, zirconium oxide is rarely used as catalyst for cross-coupling reactions.

Full text of DOI:10.1002/aoc.4396

Received: 25 December 2017
DOI: 10.1002/aoc.4396
Revised: 21 March 2018
Accepted: 23 March 2018
F U L L P A P E R
Zirconium oxide complex anchored on boehmite
nanoparticles as highly reusable organometallic catalyst for
C–S and C–O coupling reactions
Arash Ghorbani‐Choghamarani
| Zeinab Seydyosefi | Bahman Tahmasbi
Department of Chemistry, Ilam
Boehmite nanoparticles were prepared by a simple and inexpensive procedure
in water using commercially available materials without inert atmosphere.
Then, the surface of the boehmite nanoparticles was modified using 3‐
mercaptopropyltrimethoxysilane and subsequently zirconium oxide was sup-
ported on the modified surface. Zirconium oxide supported on boehmite nano-
particles (Pr.S‐ZrO@boehmite) was characterized using scanning electron
microscopy, Fourier transform infrared spectroscopy, thermogravimetric anal-
ysis and inductively coupled plasma technique. The catalytic application of Pr.
S‐ZrO@boehmite was studied in C–O and C–S coupling reactions for synthesis
of valuable compounds such as ether and sulfide derivatives. All products were
obtained in good to excellent yields and the catalyst could be recovered and
reused several times without significant loss of catalytic efficiency. Further-
more, zirconium oxide is rarely used as catalyst for cross‐coupling reactions.
University, PO Box 69315516, Ilam, Iran
Correspondence
Arash Ghorbani‐Choghamarani,
Department of Chemistry, Ilam
University, PO Box 69315516, Ilam, Iran.
Email: arashghch58@yahoo.com;
a.ghorbani@mail.ilam.ac.ir
Funding information
Ilam University
KEYWORDS
boehmite nanoparticles, C–O and C–S coupling reactions, ethers, sulfides, zirconium oxide
1
| INTRODUCTION
using simple procedures, they are used as absorbents,
vaccine adjuvants, coatings, optical material, cosmetic
The recovery and recycling of catalysts are important fac-
tors in green chemistry and industrial applications.
Recently to develop this issue, homogeneous catalysts
have been supported on various solid materials such as
products, composite reinforcement material in ceramics,
[
1–3]
pillared clays and sweep‐flocculation for freshwater treat-
[19–21]
ment, and also rarely used as supports for catalysts.
For these reasons, many methods have been reported for
the preparation of BNPs, but these reports focused on
[
4–6]
[7]
magnetic nanoparticles,
mesoporous materials, car-
[8]
[9,10]
[22–24]
bon
nanofibres,
nanotubes,
ionic
liquids,
peptide
physical and chemical properties of BNPs.
[
11]
[12]
[13]
polymers,
graphene oxide
and
Therefore in continuation of our studies of the appli-
[14]
[25,26]
heteropolyacids.
Boehmite nanoparticles (BNPs) are a
cation of boehmite as an insoluble support,
here
novel solid support that has been rarely used as a catalyst
we report a complex of zirconium oxide that is
immobilized on BNPs (Pr.S‐ZrO@boehmite). This
catalyst was used for C–S and C–O coupling reactions.
The formation of C–S and C–O bonds are great demand
in organic chemistry for the production of several impor-
tant pharmaceutical and biological compounds and there
are several reports for the synthesis of these com-
[15]
support.
High surface area, high stability in harsh con-
ditions and high density of hydroxyl groups on the
boehmite surface are unique properties of BNPs for their
[16,17]
catalytic applications.
More important, BNPs are a
suitable support for heterogenization of catalysts due to
[
16,18]
the high thermal and chemical stability of BNPs.
Because BNPs are prepared with commercial materials
[
27–32]
pounds.
Sulfides are used as potent drugs for the
Appl Organometal Chem. 2018;e4396.
wileyonlinelibrary.com/journal/aoc
Copyright © 2018 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4396

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GHORBANI‐CHOGHAMARANI ET AL.
treatment of HIV, cancer, Alzheimer's disease and
3 | RESULTS AND DISCUSSION
[11]
Parkinson's disease.
Sulfides are used as important
materials for the synthesis of sulfoxide and sulfone
derivatives.
In continuation of our studies of development of hetero-
[5]
[25,26]
geneous catalysts,
herein we modified BNPs using
MPTMS and used them as an efficient insoluble support
for zirconium oxide (Scheme 1). This is the first report
of the modification of BNPs using MPTMS. Also, zirco-
nium oxide has rarely been applied as a catalyst for the
synthesis of sulfide and ether derivatives.
2
2
| EXPERIMENTAL
.1 | Preparation of Catalyst
Initially,
BNPs
modified
using
3‐
mercaptopropyltrimethoxysilane (MPTMS) were pre-
[
17]
pared according to a newly reported procedure.
For
the preparation of Pr.S‐ZrO@boehmite, the BNPs modi-
fied using MPTMS (1.0 g) were dispersed in ethanol and
mixed with 2.5 mmol of ZrOCl ⋅8H O. The mixture was
2
2
stirred at 80 °C for 20 h. The solid product (Pr.S‐
ZrO@boehmite) was obtained after washing with ethanol
and drying at 50 °C.
2.2 | General Procedure for Synthesis of
Diaryl Sulfides and Diaryl Ethers
A round‐bottom flask was charged with 1.2 mmol of thio-
urea or 1 mmol of phenols, with aryl halide (1 mmol),
KOH (6 mmol), Pr.S‐ZrO@boehmite (40 mg, 6.2 mol%)
and dimethylsulfoxide (DMSO; 3 ml). Then the reaction
mixture was stirred at 130 °C. The progress of reaction
was observed by TLC. After completion of the reaction,
the mixture was extracted with ethyl acetate. The organic
layer was dried with anhydrous Na SO , and organic sol-
SCHEME 1 Synthesis of Pr.S‐ZrO@boehmite
2
4
vent was evaporated to afford pure products.
2.3 | Selected Spectral Data
1
Phenyl(p‐tolyl)sulfane (Table 2, entry 4). H NMR
300 MHz, CDCl , δ, ppm): 2.30 (s, 3H), 6.99–7.07 (m,
(
3
2
H), 7.14–7.20 (m, 4H), 7.23–7.32 (m, 2H), 7.53–7.56 (m,
1
H).
(
3‐Methoxyphenyl)(phenyl)sulfane (Table 2, entry
1
9
6
7
). H NMR (300 MHz, CDCl , δ, ppm): 3.71 (s, 3H),
3
.86–6.89 (m, 2H), 7.16–7.18 (m, 1H), 7.25–7.35 (m, 4H),
.35–7.37 (m, 2H).
1
‐Methoxy‐3‐phenoxybenzene (Table 4, entry 9).
1
H NMR (300 MHz, CDCl , δ, ppm): 3.72 (m, 3H), 6.51–
3
6
1
7
.55 (m, 1H), 6.56–6.57 (m, 1H), 6.71–9.72 (d, J = 4 Hz,
H), 6.99–7.02 (m, 2H), 7.11–7.15 (t, J = 6 Hz, 1H),
.23–7.29 (t, J = 8 Hz, 1H), 7.35–7.40 (m, 2H).
1
‐Methoxy‐4‐phenoxybenzene (Table 4, entry 11).
1
H NMR (300 MHz, CDCl , δ, ppm): 3.71 (s, 3H), 6.53–
3
6
7
.58 (m, 2H), 6.69–6.72 (m, 1H), 6.89–7.05 (m, 3H),
.11–7.15 (m, 1H), 7.26–7.40 (m, 2H).
FIGURE 1 SEM image of Pr.S‐ZrO@boehmite

GHORBANI‐CHOGHAMARANI ET AL.
3 of 8
Pr.S‐ZrO@boehmite was characterized using scan-
ning electron microscopy (SEM), Fourier transform
infrared (FT‐IR) spectroscopy, thermogravimetric
analysis (TGA), CHNS elemental analysis, and induc-
tively coupled plasma (ICP) analysis. SEM was used
for evaluation of particles size. As shown in
Figure 1, these nanoparticles were formed at a
nanometre size (35–50 nm) with quite homogeneous
size and shape.
and nitrate impurity were indicated by two bands at
1080 and 1634 cm , respectively. Symmetric and
asymmetric vibrations of the surface hydroxyl groups
−
1
−
1 [17]
were observed above 3000 cm
.
C─H stretching
−
1
vibration bands were observed at 2880–2980 cm in
the FT‐IR spectra of Pr.SH@boehmite and Pr.S‐
ZrO@boehmite.
After synthesis and characterization of the cata-
lyst, the application of this catalyst was studied in
C─S and C─O coupling reactions (Scheme 2). In
order to determine the best reaction conditions,
various parameters were examined in the coupling
of iodobenzene with thioacetamide as the source
of sulfur. Therefore, the sample reaction was
examined in the presence of various amounts of
Pr.S‐ZrO@boehmite (Table 1, entries 5–8) and
ICP analysis was employed for the determination of
the amount of zirconium loaded on the BNPs. According
to the ICP analysis, the exact amount of zirconium
−
3
−1
immobilized on BNPs is 1.55 × 10 mol g . In order
to obtain the ratio of zirconium to sulfur in the catalyst,
CHNS analysis was performed. According to this analysis,
the amount of sulfur immobilized on BNPs is
−
3
−1
5
.2 × 10 mol g . Therefore, the ratio of zirconium to
in
various
solvents
such
as
DMSO,
sulfur in the catalyst is 1:3.
dimethylformamide (DMF), poly(ethylene glycol)
(PEG), toluene, and water (Table 1, entries 1–5).
As evident from Table 1, the best results were
obtained in DMSO using 0.04 g (6.2 mol%) of cat-
alyst. Also, the sample reaction was examined at
various temperatures (Table 1, entries 8–12) and
with different amounts of KOH (Table 1, entries
12–14). The best results were obtained using
6 mmol of KOH at 130 °C.
DTG/TGA of Pr.S‐ZrO@boehmite was used to investi-
gate organic layers coated on BNPs (Figure 2). The TGA
diagram of Pr.S‐ZrO@boehmite shows three weight
−
1
losses with a heating rate of 10 °C min in the range
5 800 °C. The first weight loss about of 10% was seen
below 100 °C due to the removal of physically adsorbed
2
[17]
solvents.
The second weight loss in the TGA diagram
(about 20%) between 150 to 700 °C corresponds to the
decomposition of organic layers. The final weight loss
about 5% may be related to the transformation of thermal
crystal phase of boehmite particles that occurs above
After optimization of the reaction conditions, the
investigation of the catalytic activity of Pr.S‐
ZrO@boehmite was extended to a wide range of aryl
halides including those electron‐donating and elec-
tron‐withdrawing functional groups. Also aryl
iodides, aryl bromides and aryl chlorides were
employed for preparation of corresponding diaryl
sulfides. Results of these studies are summarized in
Table 2. All products were obtained in good to
excellent yields.
[33]
7
00 °C.
FT‐IR spectra of BNPs, modified BNPs using
MPTMS (Pr.SH@boehmite) and Pr.S‐ZrO@boehmite
are shown in Figure 3. The FT‐IR spectra show several
−
1
stretching vibration at 480, 630 and 740 cm which
correspond to the vibration of Al─O bonds in the
[
26]
structure of BNPs.
Vibrations of hydrogen bonds
FIGURE 2 TGA/DTA curves of Pr.S‐
ZrO@boehmite

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GHORBANI‐CHOGHAMARANI ET AL.
FIGURE 3 FT‐IR spectra of (a) BNPs,
(
b) Pr.S@boehmite and (c) Pr.S‐
ZrO@boehmite
Also, in order to optimize the reaction conditions
for the synthesis of diaryl ethers, we examined the
C─O coupling of iodobenzene with phenol in the
presence of Pr.S‐ZrO@boehmite as a model reaction.
Different amounts of catalyst and various solvents
were examined (Table 3). In the C─O coupling of
iodobenzene with phenol, the best results were
obtained in DMSO using 40 mg (6.2 mol%) of Pr.S‐
ZrO@boehmite (Table 3, entry 5). Effects of tempera-
ture, type of base and amount of base were examined,
with 130 °C and 6 mmol of KOH being selected as
optimum.
In order to extend the scope of catalytic activity of
Pr.S‐ZrO@boehmite, we examined the C─O coupling
reactions for various aryl halides. The results are sum-
marized in Table 4. Various aryl iodides, bromides and
chlorides (Table 4) were successfully converted to
diaryl ethers in short reaction times and in high
yields.
SCHEME 2 Pr.S‐ZrO@boehmite‐catalysed synthesis of sulfide
and diaryl ether derivatives via C─S and C─O coupling reaction
The recoverability and reusability of Pr.S‐
ZrO@boehmite was studied in C─O and C─S coupling
reactions. To investigate this issue, iodobenzene was
selected as sample substrate. After completion of the reac-
tions, the catalyst was recovered by centrifugation and
was used again. As shown in Figure 4, Pr.S‐
ZrO@boehmite can be reused up to five times without
any significant loss of its catalytic activity in the synthesis
of diphenyl sulfide and diphenyl ether.

GHORBANI‐CHOGHAMARANI ET AL.
5 of 8
TABLE 1 Optimizing reaction conditions for synthesis of sulfide derivatives in the presence of Pr.S‐ZrO@boehmite
a
Entry
Solvent
Catalyst (mg (mol%))
Amount of KOH (mmol)
Temperature (°C)
Yield (%)
b
b
b
b
1
2
3
4
5
6
7
8
9
H
2
O
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
20 (3.1)
30 (4.6)
50 (7.7)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
6
6
6
6
6
6
6
6
6
6
6
6
5
4
Reflux
Reflux
130
130
130
130
130
130
100
80
—
—
—
—
94
40
80
94
Toluene
DMF
PEG
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
Trace
b
1
1
1
1
1
0
1
2
3
4
—
b
60
—
b
40
—
130
130
83
77
a
Isolated yield after 60 min.
b
No reaction.
TABLE 2 C─S coupling reaction for synthesis of sulfides catalysed by Pr.S‐ZrO@boehmite
a
Entry
Aryl halide
Time (min)
Yield (%)
Melting point (°C)
Reported melting point (°C)
[
[
[
[
[
34]
34]
34]
35]
35]
1
2
3
4
5
6
7
8
9
Iodobenzene
60
92
87
27
60
50
49
40
50
80
87
73
75
65
Oil
Oil
Oil
Oil
Oil
Oil
Bromobenzene
180
24 h
130
500
15
Oil
Chlorobenzene
Oil
4‐Iodotoluene
Oil
4‐Bromotoluene
Oil
[
[
34]
34]
4‐Bromonitrobenzene
4‐Chloronitrobenzene
4‐Bromochlorobenzene
3‐Bromoanisole
157–159
157–159
Oil
150–161
150–161
30
[
[
[
[
[
[
35]
35]
34]
34]
34]
36]
155
140
330
70
Oil
Oil
Oil
Oil
Oil
Oil
Oil
1
1
1
1
0
1
2
3
2‐Iodoanisole
Oil
1‐Bromo‐3‐(trifluoromethyl)benzene
4‐Iodoanisole
Oil
300
125
Oil
2‐Iodotoluene
Oil
a
Isolated yield.
An SEM image of the recovered catalyst is shown in
determining the zirconium loading amount before
and after recycling of the catalyst using ICP
analysis. Based on such analysis, the amounts of
zirconium in fresh and reused catalyst are
1.55 and 1.41 mmol g , respectively, which shows
that zirconium leaching from Pr.S‐ZrO@boehmite
is very low.
Figure 5. Particles of the recovered catalyst were observed with
sizes between 35 and 50 nm with homogeneous nature and
cubic orthorhombic structures. Therefore, the size and shape
of catalyst particles have not been changed after recycling.
Also, the amounts of zirconium leaching after
recycling of Pr.S‐ZrO@boehmite were studied by
−
1

6
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GHORBANI‐CHOGHAMARANI ET AL.
TABLE 3 Optimizing reaction conditions for synthesis of diaryl ether derivatives in the presence of Pr.S‐ZrO@boehmite
a
Entry Solvent Catalyst (mg (mol%)) Base
Amount of base (mmol) Temperature (°C) Time (min) Yield (%)
b
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
DMF
PEG
40 (6.2)
40 (6.2)
KOH
KOH
KOH
KOH
KOH
KOH
KOH
KOH
6
6
6
6
6
6
6
6
6
6
6
5
4
3
6
6
6
6
130
130
Reflux
Reflux
130
130
130
130
130
130
130
130
130
130
100
80
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
—
—
—
—
90
58
72
90
—
—
—
88
70
58
b
b
b
Toluene 40 (6.2)
H
2
O
40 (6.2)
40 (6.2)
20 (3.1)
30 (4.6)
50 (7.7)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
40 (6.2)
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
b
b
b
K
2
CO
3
0
1
2
3
4
5
6
7
8
Na
Et
2
CO
3
3
N
KOH
KOH
KOH
KOH
KOH
KOH
KOH
Trace
b
—
b
60
—
b
40
—
a
Isolated yield.
b
No reaction.
TABLE 4 C─O coupling reaction for synthesis of diaryl ethers catalysed by Pr.S‐ZrO@boehmite
a
Entry
Aryl halide
Time (min)
Yield (%)
Melting point (°C)
Reported melting point (°C)
[
[
[
37]
37]
37]
1
2
3
4
5
6
7
8
9
Iodobenzene
160
450
24 h
30
90
85
25
75
50
82
71
80
72
75
70
Oil
Oil
Oil
Oil
Bromobenzene
Oil
Chlorobenzene
Oil
[
37]
4‐Bromonitrobenzene
4‐Bromochlorobenzene
4‐Iodotoluene
55–57
Oil
57–59
[
37]
60
Oil
Oil
[
38]
420
40
Oil
[
37]
4‐Chloronitrobenzene
4‐Bromotoluene
3‐Bromoanisole
4‐Iodoanisole
55–57
Oil
57–59
[
[
[
[
38]
510
370
12 h
55
Oil
Oil
Oil
Oil
38]
37]
37]
Oil
1
1
0
1
Oil
4‐Bromoanisole
Oil
a
Isolated yield.
The efficiency of Pr.S‐ZrO@boehmite for C─S cou-
terms of price, non‐toxicity, activity, stability and ease
of separation. Also this catalyst can be reused and the
average isolated yield for five successive runs is more
than 90%, which clearly demonstrates the practical
recyclability of this catalyst.
pling reactions was compared with previous literature
for the coupling of iodobenzene with sulfur. The
results of this comparison are presented in Table 5.
Pr.S‐ZrO@boehmite is better than other catalysts in

GHORBANI‐CHOGHAMARANI ET AL.
7 of 8
4
| CONCLUSIONS
In summary, a new complex of zirconium supported on
modified BNPs (Pr.S‐ZrO@boehmite) is reported as a
novel, highly reusable and stable catalyst for C─S and
C─O coupling reactions. This catalyst can be recovered
and reused for several cycles without loss of its catalytic
activity. The advantage of this catalyst is its simple prep-
aration using commercially available, eco‐friendly and
cheap materials. Also, nano‐boehmite is new support for
heterogenization of homogeneous catalysts. Diaryl sul-
fides and diaryl ethers were obtained in high yields in
the presence of Pr.S‐ZrO@boehmite.
ACKNOWLEDGEMENT
This work was supported by the research facilities of Ilam
University, Ilam, Iran.
FIGURE 4 Recycling experiments of Pr.S‐ZrO@boehmite in
synthesis of (a) diphenyl sulfide and (b) diphenyl ether
ORCID
Arash Ghorbani‐Choghamarani
002-7212-1317
http://orcid.org/0000-
0
Bahman Tahmasbi http://orcid.org/0000-0002-3605-2852
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