Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles

Article abstract of DOI:10.1002/aoc.6133

An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN₃ in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe₃O₄ nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe₃O₄ nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.

Full text of DOI:10.1002/aoc.6133

Received: 16 September 2020
DOI: 10.1002/aoc.6133
Revised: 27 October 2020
Accepted: 7 November 2020
F U L L P A P E R
Fe O @L-lysine-Pd(0) organic–inorganic hybrid: As a novel
3
4
heterogeneous magnetic nanocatalyst for chemo and
homoselective [2 + 3] cycloaddition synthesis of
5-substituted 1H-tetrazoles
1,2
3
1
Muhammad Aqeel Ashraf
| Zhenling Liu
| Cheng Li
|
1
Dangquan Zhang
1
School of Forestry, Henan Agricultural
An efficient and sustainable synthetic protocol has been presented to synthesis
and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The syn-
thetic protocol involves two-component reaction between aryl nitriles and
University, Zhengzhou, 450002, China
2
School of Environmental Studies, China
University of Geosciences, Wuhan,
430074, China
NaN in water using complex of L-lysine-palladium nanoparticles (NPs) modi-
3
3
School of Management, Henan
fied Fe O nanoparticles as magnetically separable, recyclable, and reusable
3 4
University of Technology, Zhengzhou,
450001, China
heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe O
3 4
nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted
H-tetrazoles. The advantages of this strategy include easy recovery and
Correspondence
1
Cheng Li and Dangquan Zhang, School of
Forestry, Henan Agricultural University,
Zhengzhou 450002, China.
efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3]
cycloaddition, short reaction times, and all of the reported synthetic
strategies are being performed in water as green solvent for a wide range of
substrates.
Email: zdq76@henau.edu.cn;
zhangdangquan@163.com;
dangquanzhang5698@gmail.com;
cheng23.le9674@gmail.com;
lichengzzm@163.com
K E Y W O R D S
[
2 + 3] cycloaddition, 5-substituted 1H-tetrazoles, Fe
3 4
O @L-lysine-Pd(0), green nanocatalyst,
water solvent
1
| INTRODUCTION
biodegradable materials in many different ways have
been demonstrated with efficient and effective cataly-
[
10]
The use of nanostructured heterogeneous catalysts in
organic transformations has recently been very exciting
in view of their catalytic efficiency and selectivity.
The ease of isolation and separation of the heterogeneous
catalysts from the desired organic product and the recy-
clability and reusability further enhanced the sustainabil-
sis.
L-lysine can be considered as excellent candidate
for functionalization of iron oxide nanoparticles as the
presence of an α-carboxylic, an α-amino group, and a
side-chain primary amine for coordination to transition
[
1–4]
[
11]
metals.
Generally speaking, the presence of amino
group beside carboxylic acid can accelerate the immobili-
zation process, which may be aided by the N–H group of
L-lysine, which is capable of forming a hydrogen bond
[5–7]
ity of the catalysts.
Moreover, the heterogeneous
catalysts not only catalyze the reactions on their own
but also serve as effective support for immobilization
of active catalyst and facilitate efficient magnetic
separation of catalysts for their recovery and reusabil-
[
12]
with the O–H groups on support surface.
Also, the
final complex can be synthesized using stable interaction
between the amine group of L-lysine and the Pd atom
and catalyze the chemical reactions efficiently and with
[
8,9]
ity.
The functionalization and modification of iron
[
12]
oxide nanoparticles with various biocompatible and
high selectivity.
Appl Organomet Chem. 2020;e6133.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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ASHRAF ET AL.
The combination of two or more nitrogen atoms in
2 | EXPERIMENTAL
2.1 | Catalyst synthesis
heterocyclic structures in one molecule with the use of
combinatorial synthesis avoiding multistep synthesis and
hazardous organic solvents has been used as an effective
molecular hybridization strategy for designing novel
drug-like molecules with structural diversity and
The Fe O @L-lysine-Pd(0) magnetic nanoparticles
3
4
(MNPs) was prepared according to the our previously
[
13–15]
[32]
molecular complexity for drug discovery research.
reported method (Scheme 1).
The close correlations between the specificity of biologi-
cal activity and the structure of complex molecule
have provided the impetus to develop a molecular
hybridization strategy to access challenging target
molecules with privileged substructures inherent in
2.2 | General procedure for the synthesis
of 5-substituted 1H-tetrazole derivatives
catalyzed by Fe O @L-lysine-Pd(0) MNPs
3
4
[12,16,17]
bioactive molecules.
N-containing heterocycles
are very interesting and elegant synthetic targets and
incorporated in a number of medicinally important natu-
A mixture of aryl nitrile (1 mmol) and sodium azide
(1.3 mmol) was dissolved in water (2 mL) in the presence
of Fe O @L-lysine-Pd(0) MNPs and stirred vigorously at
[18,19]
ral products and syntheticz pharmaceuticals.
More-
3
4
ꢀ
over, the synthetic pharmaceuticals with interesting
biological activities such as antimicrobial and antitumor
inhibitors include N-containing tetrazole structural
100 C for the required time. The progress of reaction was
monitored by thin layer chromatography (TLC). After the
completion of reaction, the mixture was cooled down to
room temperature, then HCl (4 N, 10 mL) was added to
the mixture, and after blending for 30 s, the catalyst was
separated by magnetic decantation, and the product was
washed with EtOAc and water, and organic layer was
dried over anhydrous sodium sulfate (about 1.5 g). Then
the ethyl acetate was evaporated to give the desired
tetrazole derivatives.
[14,20–23]
system in their structures.
The [2 + 3] cycloaddi-
tion synthesis of tetrazoles with medicinally privileged
fused substituent at C5 provides an opportunity for the
synthesis of a library of N-heterocycles with drug-like
[24,25]
structural diversity and complexity.
Five-substituted
1
H-tetrazole heterocycles, in particular, represent a class
of medicinally important and structurally diverse
complex molecules and incorporated as core units in a
number of natural and synthetic pharmaceuticals with a
[26–28]
wide ranging potential bioactivities.
In most of the
3 | RESULTS AND DISCUSSION
3.1 | Catalytic applications
cases, tetrazole heterocycles have been synthesized by
[
3 + 2] cycloaddition of aryl nitriles with sodium azide in
[
27,29–31]
the presence of homogeneous metal catalysts.
But
in the present work, we are concerned with the
synthesis of 5-substituted 1H-tetrazole derivatives
using L-lysine-Pd(0) catalytic complex functionalized
magnetically separable nanocomposite as recyclable and
reusable catalyst. The present work is probably the first
report on the synthesis of 5-substituted 1H-tetrazole in
the water as green solvent.
The as-prepared Fe O @L-lysine-Pd(0) was previously
3
4
completely characterized as
a
novel magnetic
nanocatalyst in our laboratory using Fourier transform
infrared spectroscopy (FT-IR), X-ray diffractometer
(XRD), energy-dispersive X-ray spectroscopy (EDS),
inductively coupled plasma atomic emission spectroscopy
(ICP), wavelength dispersive X-ray (WDX), Brunauer–
SCHEME 1 Systematic synthesis of
3 4
Fe O @L-lysine-Pd(0) magnetic
nanoparticles (MNPs)

ASHRAF ET AL.
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Emmett–Teller (BET), thermogravimetric analysis
was more completely to explore the catalytic applications
of this magnetic nanocatalyst, so its catalytic applications
were absolutely extended in the [3 + 2] cycloaddition
synthesis of 5-substituted 1H-tetrazoles in green media.
(
TGA), vibrating sample magnetometer (VSM), scanning
electron microscopy (SEM), and transmission electron
[32]
microscopy (TEM) techniques.
Our goal in this report
3 4
TABLE 1 Optimization of the reaction conditions for Fe O @L-lysine-Pd(0) NPs catalyzed the [3 + 2] cycloaddition reaction of sodium
azide and benzonitrile
Catalyst
(mol %)
Temperature
( C)
Time
(h)
Yield
TOF
ꢀ
[a]
(min−1)
Entry Catalyst
Solvent
(%)
NR
NR
TON
1
2
3
4
5
6
-
-
H
2
O
Reflux
100
24
24
1
-
-
-
-
-
-
-
-
-
-
Solvent-free
Fe
3
3
O
4
4
0.30
0.30
0.30
0.02
H
H
H
H
2
2
2
2
O
O
O
O
Reflux
Reflux
Reflux
Reflux
Trace
NR
Fe
O
@L-lysine
1
Pd (OAc)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
Fe @L-lysine-
Pd(0)
2
1
67
223.33 3.88
3
O
4
1
Trace
-
-
7
8
9
1
1
1
1
1
1
1
1
1
1
3
O
4
0.05
0.10
0.20
0.25
0.30
0.35
0.30
0.30
0.30
0.30
0.30
0.30
0.30
H
H
H
H
H
2
2
2
2
2
O
O
O
O
O
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
R.T
1
1
1
1
1
1
1
1
1
1
1
1
1
41
63
83
90
99
83
90
N.R
37
68
73
88
96
820
630
415
360
330
376
300
-
13.66
10.50
6.91
6.00
5.50
4.61
5.00
-
3 4
O
3 4
O
0
1
2
3
4
5
6
7
8
9
3 4
O
3 4
O
3
O
4
EtOH
3
O
4
H
H
H
H
H
H
H
2
O:EtOH
(1:1)
3
O
4
2
O
O
O
O
O
O
3
O
4
2
2
2
2
2
45
123
226
243
293
320
2.05
3.77
4.05
4.88
5.33
3
O
4
75
3
O
4
80
3
O
4
90
3
O
4
95
Abbreviations: NPs, nanoparticles; TOF, turnover frequency; TON, turnover number.
a
Isolated yield.

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As a part of our research program on the develop-
reaction was also evaluated in the various temperatures;
the observations show that the reflux conditions provided
maximum yield of the product in short time. Therefore,
on the basis of these observations, temperature exhibited
excellent effect in terms of product yield and duration of
the reaction.
ment of environmentally benign synthetic protocol to
synthesize structurally tetrazole molecules with medici-
nally privileged heterocyclic substructures, we wish to
report an efficient and environmentally sustainable pro-
tocol to synthesize 5-substituted 1H-tetrazoles involving
pseudo-tow component reaction of aryl nitriles and
sodium azide in water mixture using L-lysine-Pd
Under the optimized reaction conditions, the reaction
was extended with various sodium azide and various aryl
nitriles possessing either electron-withdrawing or
electron-donating substituents to synthesize a library of
5-substituted 1H-tetrazoles incorporating medicinally
privileged heterocyclic substructures with a view to
explore the feasibility and scope of the present synthetic
protocol to synthesize the N-containing heterocyclic mol-
ecules. The synthesized 5-substituted 1H-tetrazoles are
presented in Table 2. As presented in Table 2, this cata-
lytic system worked very well, and various aryl nitriles
bearing both electron-donating and electron-withdrawing
functional groups give the corresponding 5-substituted
1H-tetrazole derivatives in good to excellent yields.
A plausible mechanism for [3 + 2] cycloaddition syn-
thesis of 5-substituted 1H-tetrazoles is shown in
(
0) functionalized magnetically separable Fe O NPs as
3 4
recyclable and reusable nanocatalyst. Initially, the reac-
tion of benzonitrile and NaN was selected as a model
3
reaction to optimize the reaction conditions and to
explore the feasibility of the present synthetic strategy.
It was observed that the reaction could not provide
the desired product when performed without using cata-
lyst in the presence of solvent and without solvent even
after continuous stirring the reactants at room tempera-
ture for 24 h (Table 1, Entries 1 and 2). Thus, from these
observations, it was evident that the reaction required
suitable catalyst to obtain the desired product. The reac-
tion was further performed with three nanocatalysts:
Fe O , Fe O @L-lysine, and Pd (OAc) in water as sol-
3
4
3
4
2
[
46]
vent; the use of catalyst Fe O @L-lysine-Pd(0) MNPs pro-
Scheme 2.
In the first step, interaction of nitrile group
3
4
vided comparatively better yield as compared with
obtained by using Fe O , Fe O @L-lysine and Pd (OAc)
2
with Fe O @L-lysine-Pd(0) forms intermediate A, which
3
4
accelerates the [3 + 2] cycloaddition step. Really,
Fe O @L-lysine-Pd(0) activates the nitrile groups via
3
4
3
4
catalysts (Table 1, Entries 3–5 and 11). The influence of
catalyst loading on the yield of the product was also
examined by varying the loading amounts of the catalyst.
With the observations, it was inferred that 0.30 mol %
of Fe O @L-lysine-Pd(0) nanoparticles on the basis
3
4
coordination to nitrogen and/or triple bond. Afterwards,
it enhances the electrophilic character of cyanide group,
then sodium azide reacts with this complex and produces
the intermediate B. Finally, acidic work up, affords C
which converted to D via 1,3 H-shift.
3
4
of amount of Pd in catalyst provided the maximum yield
of the product in short conversion time (Table 1, Entry
1
1). The reaction conditions were also optimized by per-
forming the reaction with Fe O @L-lysine-Pd(0) using
3.2 | Recyclability of the catalyst
3
4
ethanol, water, and water/ethanol mixture (1:1) as green
and inexpensive solvents and observed that water pro-
vided better results (Table 1, Entries 11–13). The model
Reusability of the catalyst was also examined. For confir-
mation of a real heterogeneous catalysis, the supported
SCHEME 2 Plausible mechanism for
the [3 + 2] cycloaddition synthesis of
5
-substituted 1H-tetrazoles in the presence
of Fe @L-lysine-Pd(0) magnetic
nanoparticles (MNPs)
3 4
O

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ASHRAF ET AL.
FIGURE 1 Reusability study of the Fe
and NaN
3
O
4
@L-lysine-Pd(0) magnetic nanoparticles (MNPs) in the [3 + 2] cycloaddition of benzonitrile
3
as a model reaction in the synthesis of 5-substituted 1H-tetrazoles
catalyst is not supposed not leaching into the reaction
mixture, and the recyclability of the catalyst is highly
important. To confirm these properties, the reaction of
benzonitrile and NaN3 was selected again as model
nanoparticles with L-lysine-Pd(0) enhanced catalytic
efficiency and facilitated the reaction with excellent
yields of the reaction products. The sustainability of the
catalyst has been demonstrated by its reuse for subse-
quent reaction cycles without an appreciable lose in its
activity. The present synthetic protocol with its special
features, synthetic efficiency, operational simplicity, atom
and step economy, and environmental sustainability
including easy separation of heterogeneous catalyst, is
expected to provide an environmentally sustainable
versatile and economically viable synthetic methodology
to access a large library of drug-like small molecules
with structural diversity and molecular complexity with
excellent scope.
(Figure 1). A model reaction was preformed 10 times
with recycled catalyst. The model reaction proceeded
smoothly using recovered catalyst and without any need
to reload the under optimal reaction conditions. After
eight consecutive runs, nonappreciable loss of yields of
product, thus, no considerable loss inactivity of catalyst
was observed. Furthermore, only small difference in the
Pd content for the fresh and reused catalyst, after the
1
0 runs, was only 1.26%, proving a low rate of leaching
(Figure 1).
DATA AVAILABILITY STATEMENT
The data that support the findings of this study are avail-
able from the corresponding author upon reasonable
request.
4
| CONCLUSION
In conclusion, we have developed an efficient and sus-
tainable synthetic protocol to {3 + 2] cycloaddition syn-
thesis of a wide library of 5-substituted 1H-tetrazole
derivatives with privileged heterocyclic substructures
involving pseudo-tow component reaction of sodium
azide and various aryl nitriles possessing either electron-
withdrawing or electron-donating substituents in
water mixture using L-lysine-Pd(0) catalytic complex
functionalized Fe O nanoparticles as magnetically sepa-
rable and reusable heterogeneous catalyst. The synthesis
of 5-substituted 1H-tetrazoles with medicinally privileged
substructures using magnetically separable Fe O @L-
lysine-Pd(0) MNPs is probably the first report and not
appeared in the literature. The modification of Fe O4
AUTHOR CONTRIBUTIONS
Muhammad Aqeel Ashraf : Conceptualization; investi-
gation; methodology; software. Zhenling Liu: Data
curation; investigation; methodology; software.
ORCID
Muhammad Aqeel Ashraf https://orcid.org/0000-0003-
4916-6530
Zhenling Liu https://orcid.org/0000-0001-5036-9330
Cheng Li https://orcid.org/0000-0003-4924-2361
Dangquan Zhang https://orcid.org/0000-0003-4234-
0487
3
4
3
4
3

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1H-tetrazoles. Appl Organomet Chem. 2020;e6133.
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