First report of the direct supporting of palladium–arginine complex on boehmite nanoparticles and application in the synthesis of 5-substituted tetrazoles

Article abstract of DOI:10.1002/aoc.3644

Boehmite nanoparticles are aluminium oxide hydroxide (γ-AlOOH) particles, which were prepared using a simple and inexpensive procedure in water at room temperature and further modified using arginine. Subsequently palladium particles were immobilized on their surface to prepare Pd-Arg@boehmite. This novel nanostructured compound was fully characterized using thermogravimetric analysis, X-ray diffraction, inductively coupled plasma optical emission (ICP-OES) and energy-dispersive X-ray spectroscopies, and scanning and transmission electron microscopies. Finally, this catalyst was applied as a moisture- and air-stable heterogeneous material for the synthesis of 5-substituted 1H–tetrazole derivatives. The leaching of palladium and heterogeneity of the catalyst were studied using hot filtration and ICP-OES. This catalyst demonstrated remarkable recyclability. The novelty of this work is that it represents the first time an amino acid has been grafted on boehmite nanoparticles.

Full text of DOI:10.1002/aoc.3644

Received: 22 July 2016
DOI 10.1002/aoc.3644
Revised: 28 August 2016
Accepted: 3 September 2016
F U L L PA P E R
First report of the direct supporting of palladium–arginine
complex on boehmite nanoparticles and application in the
synthesis of 5‐substituted tetrazoles
Bahman Tahmasbi | Arash Ghorbani‐Choghamarani
Department of Chemistry, Faculty of Science, Ilam
Boehmite nanoparticles are aluminium oxide hydroxide (γ‐AlOOH) particles, which
University, PO Box 69315516, Ilam, Iran
were prepared using a simple and inexpensive procedure in water at room tempera-
Correspondence
A. Ghorbani‐Choghamarani, Department of
Chemistry, Ilam University, PO Box 69315516,
ture and further modified using arginine. Subsequently palladium particles were
immobilized on their surface to prepare Pd‐Arg@boehmite. This novel nanostruc-
tured compound was fully characterized using thermogravimetric analysis, X‐ray
Ilam, Iran.
Email: arashghch58@yahoo.com;
a.ghorbani@mail.ilam.ac.ir
diffraction, inductively coupled plasma optical emission (ICP‐OES) and
energy‐dispersive X‐ray spectroscopies, and scanning and transmission electron
microscopies. Finally, this catalyst was applied as a moisture‐ and air‐stable hetero-
geneous material for the synthesis of 5‐substituted 1H–tetrazole derivatives. The
leaching of palladium and heterogeneity of the catalyst were studied using hot filtra-
tion and ICP‐OES. This catalyst demonstrated remarkable recyclability. The novelty
of this work is that it represents the first time an amino acid has been grafted on
boehmite nanoparticles.
KEYWORDS
5‐substituted 1H–tetrazole, arginine, boehmite nanoparticles, nitrile, palladium
1
|
INTRODUCTION
corresponding nitriles. Based on this method, several proce-
dures have been reported. Unfortunately, most of them suffer
Tetrazoles are an important class of heterocycles with wide
range of applications in coordination chemistry as ligands,
in medicinal chemistry as stable surrogates for carboxylic
acids, in catalysis technology, in organometallic chemistry
as effective stabilizers of metallopeptide structures, in mate-
rial chemistry as explosives, rocket propellants, etc., and in
agriculture.[1–5] Tetrazoles can be used as isosteric replace-
ments for carboxylic acids in drug design[6] and have found
use in various material sciences, including photography and
information recording systems.[7] Also, tetrazoles and their
derivatives have been reported as analgesic, antifungal, anti‐
inflammatory, antibacterial, antiviral and anti‐proliferative
agents, potential anti‐HIV drug candidates and herbicidal
and anticancer agents.[8–10] Valsartan and losartan are two
typical examples of the extensive application of these
compounds in drugs, such as antihypertensive sartan family
drugs.[11] Conventional synthesis of 5‐substituted 1H–
tetrazoles is by [3 + 2] cycloaddition of azides to the
from some disadvantages such as: the use of organic solvents,
severe reaction conditions, water sensitivity, long reaction
time and difficulty in separation and recovery of cata-
lysts.[12,13] Thus, the development of inexpensive and envi-
ronmentally friendly alternatives for the synthesis of
tetrazoles is desirable. Therefore, to improve the stability
and reusability of environmental catalysts and remove
organic solvents from organic reactions, our attention is
focused on the development of inexpensive and available het-
erogeneous catalysts.[14,15]
Therefore, herein we report
a palladium–arginine
complex immobilized directly on boehmite nanoparticles
(Pd‐Arg@boehmite); this is found to be a stable, efficient
and highly reusable nanocatalyst for the synthesis of
5‐substituted 1H–tetrazole derivatives using nitriles and
sodium azide in PEG‐400. Because boehmite nanoparticles
are not air‐ or moisture‐sensitive, nanoboehmite was prepared
using commercially available materials such as Al(NO3)
Appl Organometal Chem 2016; 1–7
wileyonlinelibrary.com/journal/aoc
Copyright © 2016 John Wiley & Sons, Ltd.
1

2
TAHMASBI AND GHORBANI‐CHOGHAMARANI
3⋅9H2O and NaOH in water at room temperature without inert
atmosphere.[16] Recently boehmite nanoparticles have been
used as cosmetic products, absorbents, optical material, coat-
ings and composite reinforcement material in ceramics.[17,18]
Boehmite nanoparticles have several advantages such as non‐
toxicity, high specific surface area (>120 m2 g−1), stability,
ease of surface modification due to many hydroxyl groups
on their surface, high dispersion of the active phases, inex-
pensiveness and easy and ready availability.[19–21] But
nanoboehmite is rarely used as a heterogeneous support for
the immobilization of homogeneous catalysts.[22–24] Previous
studies employed a linkage or silica layer for immobilization
of catalyst on the boehmite surface; this work represents the
first time that a catalyst has been immobilized directly on
boehmite nanoparticles.
3 | RESULTS AND DISCUSSION
3.1 | Catalyst preparation
Pd‐Arg@boehmite was prepared using the concise route
outlined in Scheme 1. For this purpose, boehmite
nanoparticles were prepared via addition of NaOH to a solu-
tion of Al(NO3)3⋅9H2O as source of aluminium at room tem-
perature, and, further, a novel type of palladium–arginine
complex was immobilized directly on their surface. Two
major novelties of this work are: (1) this is the first time that
an amino acid has been immobilized directly on boehmite
nanoparticles and (2) this is the first report of Pd‐
Arg@boehmite for use as a reusable organometallic catalyst.
3.2 | Catalyst characterization
The catalyst was characterized using transmission electron
microscopy (TEM), scanning electron microscopy
(SEM), energy‐dispersive X‐ray spectroscopy (EDS),
thermogravimetric analysis (TGA), X‐ray diffraction (XRD)
and inductively coupled plasma atomic emission spectros-
copy (ICP‐OES).
Figure 1 shows the size of synthesized particles as visual-
ized using SEM (Figure 1a,b) and TEM (Figure 1c). As
shown in these images, the size and morphology of boehmite
and Pd‐Arg@boehmite particles are quite homogeneous with
obtained diameter in the range 20–25 nm. The SEM images
of boehmite and catalyst are in good agreement with each
other in terms of particle size and shape.
2
| EXPERIMENTAL
2.1 | Preparation of catalyst
A solution of NaOH (6.490 g) in 50 ml of distilled water was
added dropwise to a solution of Al(NO3)3⋅9H2O (20 g) in
30 ml of distilled water under vigorous stirring. The resulting
milky mixture was subjected to mixing in an ultrasonic bath
for 3 h at 25 °C. The resulting nano aluminium oxyhydroxide
was filtered and washed with distilled water and kept in an
oven at 220 °C for 4 h. The thus obtained boehmite
nanoparticles (1.5 g) were dispersed in 50 ml of deionized
water, and then 2.5 mmol of L‐arginine was added to the mix-
ture. The reaction mixture was stirred at 90 °C for 24 h. Then,
the prepared nanoparticles (Arg@boehmite) were filtered,
washed with ethanol and dried at room temperature.
Arg@boehmite (0.5 g) was then dispersed in 25 ml of etha-
nol, and palladium acetate (0.25 g) was added to the reaction
mixture. The reaction mixture was stirred at 80 °C for 20 h.
NaBH4 (0.3 mmol) was added and the reaction was allowed
to run for another 2 h. The final product (Pd‐Arg@boehmite)
was filtered, washed with ethanol and dried at room
temperature.
In order to determine the kinds of elements present in the
catalyst, EDS analysis of Pd‐Arg@boehmite was performed.
2.2 | General procedure for preparation of tetrazole
derivatives
A mixture of nitrile (1 mmol) and sodium azide (1.4 mmol) in
the presence of 0.025 g of Pd‐Arg@boehmite was stirred at
120 °C in poly(ethylene glycol) (PEG). After completion of
the reaction (observed using TLC), the reaction mixture was
cooled to room temperature. The catalyst was removed by
simple filtration and HCl (4 N, 10 ml) added to the filtered
solution and corresponding tetrazole extracted with ethyl ace-
tate (2 × 10 ml). The resultant organic layer was washed with
distilled water, dried over anhydrous sodium sulfate and
concentrated to afford the crude solid product.
SCHEME 1 Synthesis of Pd‐Arg@Boehmite

TAHMASBI AND GHORBANI‐CHOGHAMARANI
3
The EDS pattern of Pd‐Arg@boehmite is shown in
Figure 1(d). The EDS spectrum of the catalyst indicates
the presence of Al, O, C, N and Pd species in the catalyst.
Also, upon complexation of the modified boehmite
nanoparticles with palladium, the exact amount of metal
loading was determined using ICP‐OES. Based on this anal-
ysis, the amount of Pd in the Pd‐Arg@boehmite is about
1.35 × 10−3 mol g−1
.
The XRD patterns of boehmite nanoparticles and
Pd‐Arg@boehmite are presented in Figure 2(I). The boehm-
ite phase is characterized by peaks at 2θ values of 14.40°,
28.41°, 38.55°, 46.45°, 49.55°, 51.94°, 56.02°, 59.35°,
65.04°, 65.56°, 68.09° and 72.38° in the XRD patterns, these
peaks being related to (0 2 0), (1 2 0), (0 3 1), (1 3 1), (0 5 1),
(2 0 0), (1 5 1), (0 8 0), (2 3 1), (0 0 2), (1 7 1) and (2 5 1)
reflections, respectively, which is in a good agreement with
standard boehmite XRD spectrum and the all peaks confirm
the crystallization of boehmite with an orthorhombic unit
cell.[22,25] Also, it can be seen that the boehmite phase is
not destroyed during the modifications.
Quantitative determination of the organic groups loaded
on the surface of nanoparticles was studied using TGA
(Figure 2II). Three main peaks can be seen in these curves.
The first one, appearing at low temperature, shows a weight
loss of 10% and is probably related to the physically adsorbed
solvent on the surface of particles.[23,26] The second one
appears in the temperature range 250–600 °C and is related
FIGURE
1
SEM images of (a) boehmite nanoparticles and (b) Pd‐
Arg@boehmite. (c) TEM image of Pd‐Arg@boehmite. (d) EDX spectrum
of Pd‐Arg@boehmite
FIGURE 2 (I) XRD patterns of (a) boehmite nanoparticles and (b) Pd‐
Arg@boehmite. (II) TGA/DTA curves of Pd‐Arg@boehmite

4
TAHMASBI AND GHORBANI‐CHOGHAMARANI
to the organic groups and palladium complex immobilized on
boehmite nanoparticles. This peak shows a weight loss of 9%.
The final weight loss of about 3% between 700 and 800 °C
may be associated with the transformation of thermal crystal
phase of boehmite particles.
product or reaction time. Also, the effect of solvent was
examined. When PEG‐400 is used as solvent (Table 1,
entry 3), excellent yield of product (97% within 7 h) is
obtained, while no detectable reaction is observed in
dichloromethane and acetone (Table 1, entries 11 and 12).
Further, in water and ethanol, only small amounts of product
form (28–32%; Table 1, entries 9 and 10) and, in the case of
dimethylsulfoxide (DMSO) and dimethylformamide (DMF)
conversion is achieved up to 80% (Table 1, entries 7 and 8).
Therefore, inferior results are obtained in dichloromethane,
acetone, DMSO, DMF, water and ethanol (Table 1, entries
7–12). As evident from Table 1, the effect of temperature
(entries 12–14) and amount of NaN3 (entries 1–3) were also
studied and the best results are obtained at 120 °C using
1.4 mmol of NaN3 (97%; Table 1, entry 3), while conversion
reduced to 69% using 1.3 mmol of NaN3 (Table 1, entry 2).
Therefore, 0.025 g of Pd‐Arg@boehmite in PEG‐400 using
1.4 mmol of NaN3 at 120 °C are found to be the best reaction
conditions for the synthesis of tetrazoles.
On the basis of the above results, the catalytic activity of
Pd‐Arg@boehmite was further explored for various
substrates. The results are summarized in Table 2. These
results show that the reactions are equally facile with
both electron‐donating and electron‐withdrawing substituents
on the benzonitriles, and all products are obtained in good
yields. As evident from Table 2, various ortho‐, meta‐ and
para‐substituted benzonitriles were investigated for this
catalytic reaction and tetrazoles are isolated in good
yields. Interestingly, dicyano derivatives such as
3.3 | Catalytic activity of Pd‐Arg@boehmite in
synthesis of tetrazoles
After characterization of Pd‐Arg@boehmite, its application
was investigated for the synthesis of 5‐substituted 1H–
tetrazole derivatives. Synthesis of tetrazoles via [2 + 3] cyclo-
addition reaction of nitriles with sodium azide (NaN3) in the
presence of this catalyst in PEG‐400 is shown in Scheme 2.
In order to determine the best reaction conditions, the
effect of various parameters such as solvent, temperature,
amount of NaN3 and amount of catalyst were examined in
the [2 + 3] cycloaddition reaction of benzonitrile with
NaN3 (Table 1). When 15 mg of Pd‐Arg@boehmite is
employed to catalyse the [2 + 3] cycloaddition reaction of
benzonitrile with NaN3, the product is obtained in 41% yield.
Increasing the amount of Pd‐Arg@boehmite from 20 to
25 mg leads to an increase in the yield of product from 64
to 97%. Further increasing the amount of Pd‐Arg@boehmite
(from 25 to 30 mg) has no significant effect on the yield of
terephthalonitrile,
2‐benzylidenemalononitrile,
2‐(4‐
nitrobenzylidene)malononitrile and malononitrile afford the
monoadditionproduct(Table2,entries7,11,12,14).
SCHEME 2 Synthesis of 5‐substituted 1H–tetrazole derivatives in the pres-
ence of Pd‐Arg@boehmite as catalyst
TABLE 1 Optimization of reaction conditions for synthesis of 5‐substituted 1H–tetrazole derivatives in the presence of Pd‐Arg@boehmite
Entry
Catalyst (mg)
Solvent
NaN3 (mmol)
Temperature (°C)
Time (h)
Yield (%)a
1
25
25
25
30
20
15
25
25
25
25
25
25
25
25
PEG
PEG
1.2
1.3
1.4
1.4
1.4
1.4
1.4
1.4
1.4
1.4
1.4
1.4
1.4
1.4
120
120
7
64
69
2
7
3
PEG
120
7
97
4
PEG
120
6.5
7
96
5
PEG
120
64
6
PEG
120
7
41
7
DMSO
DMF
H2O
120
6.3
6
90
8
120
93
9
Reflux
Reflux
Reflux
Reflux
100
7
28
10
11
12
13
14
EtOH
Acetone
CH2Cl2
PEG
7
32
7
Trace
Trace
69
7
7
PEG
80
7
35
aIsolated yield.

TAHMASBI AND GHORBANI‐CHOGHAMARANI
5
TABLE 2 Synthesis of 5‐substituted 1H–tetrazole derivatives in the presence of Pd‐Arg@boehmite
Entry
Nitrile
Time (h)
Yield (%)a
M.p. (°C)
Ref.
[28]
[9]
1
Benzonitrile
4‐Nitrobenzonitrile
7
3
97
96
90
91
91
90
85
89
95
90
73
75
74
91
69
78
214–216
217–220
173–176
129–132
180–183
224–226
254–257
149–152
233–235
261–263
167–169
162–165
119–122
115–117
245–248
229–232
2
[27]
[27]
[27]
[27]
[9]
3
4‐Acetylbenzonitrile
3‐Chlorobenzonitrile
2‐Chlorobenzonitrile
2‐Hydroxybenzonitrile
Terephthalonitrile
24
8
4
5
3
6
7
7
6
[27]
[9]
8
3‐Nitrobenzonitrile
8
9
4‐Hydroxybenzonitrile
4‐Chlorobenzonitrile
2‐Benzylidenemalononitrile
2‐(4‐Nitrobenzylidene)malononitrile
2‐Phenylacetonitrile
4
[9]
10
11
12
13
14
15
16
5
[27]
[27]
[9]
24
22
24
3
[8]
Malononitrile
[35]
[31]
[1,1′‐Biphenyl]‐4‐carbonitrile
4‐Methoxybenzonitrile
24
26
aIsolated yield.
A plausible mechanism for the synthesis of tetrazoles in
the presence of Pd‐Arg@boehmite is shown in Scheme 3.
Initially, the catalyst reacts with C N bond in nitrile to pro-
duce intermediate I; the [3 + 2] cycloaddition interaction of
C N bond in nitrile with azide ion takes place to afford
intermediate II. The protonolysis of intermediate II by
HCl gives III, which rearranges to produce more stable
desired product IV and catalyst is regenerated at the end
of the reaction.
palladium leaching (Figure 3). The average isolated yield is
obtained as 94%, which shows the practical reusability of this
catalyst.
3.5 | Catalyst leaching study
Leaching of palladium from Pd‐Arg@boehmite was studied
using ICP‐OES and the hot filtration test. Based on the
results from ICP‐OES analysis, the amount of palladium in
fresh catalyst and the catalyst after six recycles is 1.35 and
1.26 mmol g−1, respectively, which indicates that leaching
of palladium from this catalyst is very low.
3.4 | Recyclability of Pd‐Arg@boehmite
The recyclability of Pd‐Arg@boehmite was examined in the
synthesis of 5‐(4‐nitrophenyl)‐1H–tetrazole under the opti-
mized conditions. The catalyst was reused for up to six runs
without any significant loss of its catalytic activity or
In order to conduct the hot filtration experiment, two
reactions of 4‐hydroxybenzonitrile with NaN3 were
performed under optimized conditions. In the first reaction,
the synthesized 4‐(1H–tetrazol‐5‐yl)phenol was isolated after
SCHEME 3 Plausible mechanism for the synthesis of tetrazoles catalysed
by Pd‐Arg@boehmite
FIGURE 3 Recyclability of Pd‐Arg@boehmite in the synthesis of 5‐(4‐
nitrophenyl)‐1H–tetrazole

6
TAHMASBI AND GHORBANI‐CHOGHAMARANI
TABLE 3 Comparison of results for Pd‐Arg@boehmite with those for other catalysts in synthesis of 5‐phenyl‐1H‐tetrazole
Entry
Catalyst
Condition
Time (h)
Yield (%)a
Ref.
[27]
[31]
[32]
[30]
[33]
[34]
[35]
[4]
1
CoY zeolite
Cu–Zn alloy nanopowder
B(C6F5)3
DMF, 120 °C
DMF, 135 °C
14
10
8
90
95
94
90
81.1
86
86
98
82
79
90
97
2
3
DMF, 120 °C
4
Fe3O4@SiO2/Salen Cu(II)
Fe3O4/ZnS HNSs
Mesoporous ZnS
LiB(N3)4
DMF, 120 °C
7
5
DMF, 120 °C
24
36
8
6
DMF, 120 °C
7
NH4OAc (15 mg), DMF–MeOH (9:1), 120 °C
DMF, 120 °C
8
Cu(OAc)2
12
12
12
12
7
[29]
[36]
[37]
9
CuFe2O4
DMF, 120 °C
10
11
12
FeCl3–SiO2
DMF, 120 °C
Nano ZnO/Co3O4
Pd‐Arg@boehmite
DMF, 120–130 °C
PEG, 120 °C
This work
aIsolated yield.
2 h (the half‐time of the reaction) in the presence of catalyst
from which 44% of product was obtained after usual work‐
up. Simultaneously in the second reaction, the same process
was repeated, but at the half‐time of the reaction (after 2 h),
the catalyst was removed from the reaction mixture by filtra-
tion and the reaction mixture was allowed to run for another
2 h. The yield of the reaction in this stage was 48%. These
experiments confirm that Pd‐Arg@boehmite is essential for
completion of the reaction and leaching of palladium does
not occur.
directly on boehmite nanoparticles. This catalyst showed high
reusability, excellent catalytic activity and air‐ and or mois-
ture‐stability for the synthesis of 5‐substituted 1H–tetrazole
derivatives in PEG‐400. The advantages of this protocol are
the use of chemically stable and commercially available
materials, eco‐friendliness, operational simplicity and good
to high yields, and, more importantly, the catalyst can be syn-
thesized from inexpensive and commercially available
starting materials. The heterogeneity of this catalyst has been
studied using hot filtration and ICP‐OES techniques.
ACKNOWLEDGEMENT
3.6 | Comparison of catalyst
This work was supported by the research facilities of Ilam
University, Ilam, Iran.
In order to examine the efficiency of Pd‐Arg@boehmite,
we compared the results for the synthesis of 5‐phenyl‐
1H‐tetrazole in the presence of this catalyst with those of
catalysts previously reported in the literature (Table 3). As
is evident, this catalyst shows shorter reaction time and
better yield than the other catalysts. Also, Pd‐Arg@boehmite
is comparable in terms of cost, non‐toxicity, simple
preparation, stability and ease of separation. As evident
from Table 3, most previously reported methods have
drawbacks or limitations such as the use of hazardous organic
solvents, water sensitivity, severe reaction conditions, long
reaction times, difficulty in separation and recovery of
catalysts, and use of homogeneous catalysts that are difficult
to separate from the reaction mixture. In contrast, the
synthesis of tetrazoles in the presence of Pd‐Arg@boehmite
has been carried out in PEG as a green solvent in short
reaction time.
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SUPPORTING INFORMATION
Additional Supporting Information may be found online in
the supporting information tab for this article.
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