Simple and Practical Synthesis of Various New Nickel Boride-Based Nanocomposites and their Applications for the Green and Expeditious Reduction of Nitroarenes to Arylamines under Wet-Solvent-Free Mechanochemical Grinding

Article abstract of DOI:10.1071/CH18200

In this paper, we report a simple synthesis of four new nickel boride-based nanocomposites, namely Ni₂B@ZrCl₄, Ni₂B@Cu₂O, Ni₂B@CuCl₂ and Ni₂B@FeCl₃, from commercially available and cheap starting materials. All of the new Ni₂B-based nanocomposites were well characterized by Fourier-transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, and energy-dispersive X-ray spectroscopy. Further, the catalytic applications of these new nanocomposites were successfully evaluated in the wet-solvent-free reduction of aromatic nitro compounds to arylamines with sodium borohydride (NaBH₄) at room temperature by a mechanochemical grinding technique. All the introduced catalytic systems provide excellent yields of arylamines in very short reaction times for a wide range of substrates. Also, recoverability and reusability of the new nanocomposites were investigated.

Full text of DOI:10.1071/CH18200

CSIRO PUBLISHING
Aust. J. Chem.
Full Paper
https://doi.org/10.1071/CH18200
Simple and Practical Synthesis of Various New Nickel
Boride-Based Nanocomposites and their Applications for
the Green and Expeditious Reduction of Nitroarenes to
Arylamines under Wet-Solvent-Free Mechanochemical
Grinding
A B
,
A
A
Hossein Mousavi,
Mozhgan Esmati
Behzad Zeynizadeh, Reza Younesi, and
A
A
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia,
Iran.
B
Corresponding author. Email: 1hossein.mousavi@gmail.com
In this paper, we report a simple synthesis of four new nickel boride-based nanocomposites, namely Ni2B@ZrCl4,
Ni2B@Cu2O, Ni2B@CuCl2 and Ni2B@FeCl3, from commercially available and cheap starting materials. All of the new
Ni2B-based nanocomposites were well characterized by Fourier-transform infrared spectroscopy, X-ray diffraction,
scanning electron microscopy, and energy-dispersive X-ray spectroscopy. Further, the catalytic applications of these new
nanocomposites were successfully evaluated in the wet-solvent-free reduction of aromatic nitro compounds to arylamines
with sodium borohydride (NaBH4) at room temperature by a mechanochemical grinding technique. All the introduced
catalytic systems provide excellent yields of arylamines in very short reaction times for a wide range of substrates. Also,
recoverability and reusability of the new nanocomposites were investigated.
Manuscript received: 2 May 2018.
Manuscript accepted: 25 July 2018.
Published online:
22 August 2018.
hydroxythiocyanates,[19] synthesis of aryl toluenesulfonhy-
drazides and aryl toluenesulfonates,[20] synthesis of 1,3-dithiane
and 1,3-dithiolane derivatives,[21] preparation of 5-aryl-2-
furoyl-substituted thioureas and thiosemicarbazides,[22]
synthesis of 2,6-dicyanoanilines,[23] one-pot synthesis of 3-
Introduction
At the beginning of the new century, green chemistry was rec-
ognized as a valuable culture and protocol for achieving sus-
tainable development.[1] One of the important and effective
aspects of green chemistry is solvent choice.[2] Solvents are
often the largest sources of waste in chemical synthesis. Elim-
inating the use of solvents can significantly reduce the amount of
waste and volatile organic compounds that are produced in a
reaction process. Therefore, it can be said that the best solvent is
no solvent.[3] In recent years, the technique of mechanochemical
solid-state grinding has been recognized as an important and
exceptional green solvent-free technique in organic synthesis
not only for its solvent-free conditions but also for its time
efficiency, cleanliness, and safer reaction profile, easy handling,
high selectivity, and simple workup procedures.[4] Notably, it
is carried out easily in the absence of or with minimal use of
solvents in a mortar and pestle. Recently, various organic
transformations have been accomplished using the solid-state
grinding technique including aldol and cross-aldol condensa-
tion,[5] Biginelli reaction,[6] cyclopropanation,[7] Dieckmann
condensation,[8] Grignard reaction,[9] Hantzsch dihydropyridine
(DHP) synthesis,[10] synthesis of various heterocyclic
compounds,[11] spiro compounds,[12] benzene rings,[13] and
b-aminobutyric acids,[14] Knoevenagel condensation,[15]
Reformatsky reaction,[16] Michael reaction,[17] Passerini reac-
tion,[18] regioselective conversion of epoxides to vicinal
amino-2,4-dicarbonitrile-5-methylbiphenyl
derivatives,[24]
preparation of 2-arylidene indan-1,3-diones,[25] preparation of
5-arylidene barbituric acid derivatives,[26] synthesis of water-
soluble [60]fullerenol,[27] selective protection of primary alco-
hols and phenols,[28] synthesis of hexaalkoxytriphenylenes via
oxidative coupling trimerization of 1,2-dialkoxybenzenes,[29]
synthesis of 1-aryloxyacetyl-4-(2-benzofuroyl)semicarbazides,[30]
facile synthesis of dialkyl disulfides,[31] synthesis of
trisubstituted methanes,[32] preparation of azo dyes,[33] oxida-
tion of oximes,[34] and reduction.[35] The catalyst is another
important aspect of green chemistry.[36] Nowadays, the design
and development of new nano-based catalysts attract a great deal
of attention in synthetic organic chemistry because most of them
have fewer drawbacks than classical catalysts, such as diffi-
culties in purification of the final products, and deactivation of
the catalyst.[37] Metal nanoparticles are undoubtedly among the
most widely studied systems in modern nanoscience. Notably,
this is because metals often have totally different properties
when dispersed at nanometre dimensions. As an example, gold
nanoparticles are active catalysts for oxidation reactions
whereas the bulk metal is inactive. It should also be mentioned
Journal compilation ꢀ CSIRO 2018
www.publish.csiro.au/journals/ajc

B
H. Mousavi et al.
Ni2B@ZrCl4, NaBH4
Solvent-free, one drop H2O
Grinding, room temperature
0.5–7 min, 90–98 %
NH2
N
OH
O
O
N
CH3
H2N
NH2
HO
O
Ni2B@Cu2O, NaBH4
H3C
Iclaprim
Solvent-free, one drop H2O
Grinding, room temperature
Immediate-4 min, 85–98 %
Octopamine
NH2
NH2
Ar
NO2
Ar
Ni2B@CuCl2, NaBH4
H2N
N
H3C
O
O
Solvent-free, one drop H2O
Grinding, room temperature
Immediate-5 min, 85–98 %
S
N
N
N
N
H3C
H
N
O
HO
HO
HO
O
O
O
Ni2B@FeCl3, NaBH4
Solvent-free, one drop H2O
Grinding, room temperature
0.5–8 min, 85–98 %
OH
Vidarabine
Amprenavir
NH2
Scheme 1. Reduction of nitroarenes to arylamines using wet-solvent-free
mechanochemical grinding catalyzed by Ni2B-based nanocomposites.
NH2
O
Cl
N
H
OH
Tryptamine
Baclofen
(such as H, F, Cl, Br, I, OH, CN, B, Sn, P, CF3, SCF3) through the
corresponding diazonium salts.[43] One of the most important
and straightforward methods for the preparation of aliphatic or
aromatic amines is the reduction of nitro compounds. In recent
years, numerous protocols for the reduction of nitro-containing
compounds have been reported in the literature.[44] However,
some of the reported methods have disadvantages including
long reaction times, harsh reaction conditions, and use of toxic
solvents and harmful catalysts. Owing to the high importance of
amines and in response to the problems mentioned, designing
new synthetic methods based on green chemistry protocols
for the preparation of these valuable compounds is of great
importance.
In continuation of our research program into the design
and preparation of simple and cost-effective nanomaterials
and using them as efficient catalysts in different types of organic
reactions,[45] we report herein the convenient and affordable
synthesis of the new Ni2B-based nanocomposites Ni2B@ZrCl4,
Ni2B@Cu2O, Ni2B@CuCl2, and Ni2B@FeCl3 and their impres-
sive catalytic effects on the reduction of aromatic nitro com-
pounds to arylamines with sodium borohydride (NaBH4) at
room temperature under wet-solvent-free mechanochemical
grinding (Scheme 1).
Fig. 1. Examples of amine-containing drugs on the market.
SO3Na
NH2
H2N
SO3Na
N
N
NH2
SO3Na
H3C
ϩ
N
NH
H2N
Cl
Cl
Cl
S
N
NH2
CH3
Fig. 2. Chemical structure of some organic dyes bearing amine functional
groups.
Experimental
that earth-abundant transition-metal-based nanoparticles are
used as efficient and practical catalysts in various organic
reactions because transition metal nanoparticle species not only
mimic metal surface activation and catalysis but are also utilized
as nano-sized catalyst supports.[38]
Amines are an extremely important family of compounds in
chemical and pharmaceutical sciences. They are increasingly
present in the chemical structure of a very large number of drugs
(Fig. 1), dyes (Fig. 2), agrochemicals, polymers, and more.[39]
Also, amines play a prominent role in synthetic chemistry as
simple and efficient solvents[40] and catalysts.[41] Furthermore,
4-aminophenol oxalate salt is used as a corrosion inhibitor.[42]
Amino groups can easily be replaced by other functional groups
Reagents, Samples, and Apparatus
Chemicals were purchased from Merck, Fluka, and Sigma–
Aldrich. Melting points were determined on an Electrothermal
9200 apparatus. Infrared spectra were recorded on a Nexus 670
Thermo Nicolet Fourier-transform infrared (FT-IR) spec-
1
trometer and measured as KBr discs. H NMR spectra were
recorded on a Bruker Avance spectrometer at 300 MHz in
CDCl3 with tetramethylsilane as internal standard. X-ray dif-
fraction (XRD) measurements were done with a Philips
PANalytical X’Pert Pro powder diffractometer. Particle mor-
phology was examined using scanning electron microscopy
(SEM) with a FESEM-Tescan MIRA3.

Green Reduction of Nitroarenes to Arylamines
C
100
95
90
85
80
75
70
65
60
55
50
45
40
35
30
25
20
15
4000
3500
3000
2500
2000
1500
1000
500
Wavenumber [cmϪ1
]
Fig. 3. FT-IR spectrum of Ni2B@Cu2O.
15000
10000
5000
0
20
30
40
50
60
70
Position 2θ [deg.]
Fig. 4. XRD pattern of Ni2B@Cu2O.
Preparation of Nickel Boride (Ni2B) Nanoparticles (NPs)
Typical Procedure for the Synthesis of Ni2B-Based
Nanocomposites
Nickel boride (Ni2B) was prepared according to the litera-
ture.[46] In a dry two-necked round-bottomed flask (100 mL,
equipped with a magnetic stirrer, Ni(OAc)2.4H2O (1.244 g,
5 mmol) was dissolved in water (50 mL) under an atmosphere of
nitrogen. Then, a solution of sodium borohydride (10 mL, 1 M)
was gradually added within 30 s. The reaction is speedy and
accompanied by the release of large amounts of hydrogen gas.
On addition of the NaBH4 solution, a black precipitate was
produced. After complete removal of hydrogen gas from the
reaction environment, a solution of sodium borohydride (5 mL,
1 M) was again gradually added to the reaction mixture under
air. Finally, the black sediment was separated from the aqueous
phase and washed with absolute ethanol (2 ꢀ 25 mL), and then
was dried in air.
The preparation of Ni2B@ZrCl4 nanocomposite is presented
here as a typical procedure. To prepare the Ni2B@ZrCl4 sys-
tem, suspensions of ZrCl4 (0.43 mmol, 100 mg) and Ni2B
(0.39 mmol, 50 mg) in dichloromethane (20 mL) were pre-
pared separately. The ZrCl4 suspension was then added slowly
to the Ni2B suspension and the mixture stirred vigorously for
30 min in a round-bottomed flask (100 mL) equipped with a
magnetic stirrer. The dichloromethane was evaporated under
reduced pressure and the residue was dried in air. ZrCl4 was
deposited on Ni2B in a weight ratio of 100 : 50 respectively.
The other three new nanocomposite systems viz, Ni2B@Cu2O,
Ni2B@CuCl2, and Ni2B@FeCl3 were also synthesized
according to this procedure.

D
H. Mousavi et al.
General Procedure for the Reduction of Aromatic Nitro
Compounds to Arylamines
(a)
As a representative example, a mixture of nitrobenzene
(1 mmol), Ni2B@Cu2O (54 mg), 1 drop of distilled water, and
NaBH4 (2.5 mmol) was ground using a simple porcelain
mortar and pestle for 1 min at room temperature. After com-
pletion of the reaction (checked by TLC), distilled water
(5 mL) was added to the reaction vessel, and subsequently the
reaction mixture transferred to a round-bottom flask (25 mL)
equipped with a magnetic stirrer. The mixture was stirred
vigorously for 2 min. Next, the product was extracted with
dichloromethane (5 ꢀ 3 mL). The extracts were dried with
anhydrous sodium sulfate and then passed through a cotton
filter. Evaporation of the solvent afforded pure aniline in 98 %
yield.
Results and Discussion
Characterization of Nickel Boride (Ni2B) NPs
We used FT-IR and XRD spectra and SEM images to charac-
terize the Ni2B nanoparticles (see Supplementary Material).
Comparing these with spectra and images reported in the sci-
entific literature confirmed the synthesis of Ni2B nano-
particles.[47] The XRD spectrum of the prepared Ni2B indicates
an amorphous structure for the catalyst. The broad peak at
47.4878 is associated with fine particles with nano dimensions.
The amorphous morphology of the Ni2B powder was also
confirmed in SEM images. Stacked spherical particles were
observed in the structures. Also, the SEM images indicated that
the particles are in the nanometric range and the average particle
size is 27 nm.
SEM HV: 20.0 kV
MIRA3 TESCAN
WD: 5.09 mm
Det: SE
2 μm
View field: 14.4 μm
SEM MAG: 19.2 kx Date(m/d/y): 05/03/16
Kurdistan University
(b)
Characterization of New Nickel Boride-Based
Nanocomposites
All of the isolated new nickel boride-based nanocomposites
were characterized by FT-IR, XRD, SEM, and energy-
dispersive X-ray (EDX) spectroscopy. (For spectra and
images details, see Supplementary Material.) As an
example, in this section, the structure of Ni2B@Cu2O was
investigated based on its spectra and related images. The FT-IR
spectrum of Ni2B@Cu2O (Fig. 3) shows an absorbance peak at
621 cmꢁ1 due to CuI–O stretching, consistent with the litera-
ture.[48] The XRD spectrum (Fig. 4) contains seven peaks that
are clearly distinguishable and broad. All of the diffraction
peaks can be perfectly indexed to (110), (111), (200), (211),
(220), (311), and (222) peaks of cubic Cu2O (JCPDS nos
05–0667 and 78–2076).[49] The morphology and size of the
prepared Ni2B@Cu2O were characterized by SEM (Fig. 5).
According to the SEM micrographs of the Ni2B@Cu2O sys-
tem, deformed cubic microcrystallites of Cu2O have perme-
ated into the aggregated structure of Ni2B nanoparticles and
made a nanocomposite in which Ni2B NPs are scattered around
the Cu2O micro-crystallites. The high-magnification image
(Fig. 5b) demonstrates that the prepared Ni2B@Cu2O is
composed of small nanoparticles. Additionally, EDX analysis
from the Ni2B@Cu2O nanocomposite system obtained (Fig. 6)
showed the presence of the expected elements in the structure
of the nanocomposite, namely boron, nickel, copper, and
oxygen.
SEM HV: 20.0 kV
WD: 4.91 mm
Det: SE
MIRA3 TESCAN
Kurdistan University
500 nm
View field: 2.35 μm
SEM MAG: 118 kx Date(m/d/y): 05/03/16
Fig. 5. SEM images of Ni2B@Cu2O.
Catalytic Activity
The catalytic activity of these new nanocomposites was
tested in the reduction of aromatic nitro compounds to the
corresponding arylamines. First, we chose the reaction of
nitrobenzene with NaBH4 in the presence of a catalytic amount
of Ni2B@ZrCl4 as a model reaction. Then, we optimized the
reaction conditions using various molar ratios of sodium
borohydride as well as testing solvents such as methanol,
ethanol, ethyl acetate, tetrahydrofuran (THF), acetonitrile, and
water, and solvent-free conditions at room temperature and

Green Reduction of Nitroarenes to Arylamines
E
CuLα
2500
NiLα
2000
1500
1000
CuKα
NiKα
O Kα
500
CuKβ
NiKβ
B Kα
0
0
keV
10.00
Fig. 6. EDX spectrum of Ni2B@Cu2O.
Table 1. Optimization of reaction conditions
rt, room temperature
NH2
NO2
Nanocomposite, NaBH4
Solvent, conditions
Entry
NaBH4 [mmol]
Nanocomposite [mg]
Solvent
Conditions
H2O
Time [min]
Conversion [%]
1
3
Ni2B@ZrCl4 (72)
Ni2B@ZrCl4 (72)
Ni2B@ZrCl4 (72)
Ni2B@ZrCl4 (72)
Ni2B@ZrCl4 (72)
Ni2B@ZrCl4 (72)
Ni2B@ZrCl4 (36)
Ni2B@ZrCl4 (36)
Ni2B@ZrCl4 (72)
Ni2B@Cu2O (54)
Ni2B@Cu2O (54)
Ni2B@Cu2O (54)
Ni2B@Cu2O (54)
Ni2B@Cu2O (54)
Ni2B@Cu2O (54)
Ni2B@Cu2O (27)
Ni2B@Cu2O (27)
Ni2B@Cu2O (54)
Ni2B@CuCl2 (52)
Ni2B@CuCl2 (52)
Ni2B@CuCl2 (52)
Ni2B@CuCl2 (52)
Ni2B@CuCl2 (52)
Ni2B@CuCl2 (52)
Ni2B@CuCl2 (26)
Ni2B@CuCl2 (26)
Ni2B@CuCl2 (52)
Ni2B@FeCl3 (58)
Ni2B@FeCl3 (58)
Ni2B@FeCl3 (58)
Ni2B@FeCl3 (58)
Ni2B@FeCl3 (58)
Ni2B@FeCl3 (58)
Ni2B@FeCl3 (29)
Ni2B@FeCl3 (29)
Ni2B@FeCl3 (58)
MeOH
EtOH
EtOAc
THF
CH3CN
H2O
–
Reflux
–
100
100
100
100
100
120
60
0
0
2
3
Reflux
–
3
3
Reflux
–
0
4
3
Reflux
–
0
5
3
Reflux
–
0
6
3
Reflux
–
50
70
100
100
0
7
2
Grinding, rt
Grinding, rt
Grinding, rt
Reflux
1 drop
8
2.5
2.5
3
–
1 drop
7
9
–
1 drop
3
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
MeOH
EtOH
EtOAc
THF
CH3CN
H2O
–
–
100
100
100
100
100
120
60
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
60
70
100
100
0
2
Grinding, rt
Grinding, rt
Grinding, rt
Reflux
1 drop
2.5
2.5
3
–
1 drop
5
–
1 drop
1
MeOH
EtOH
EtOAc
THF
CH3CN
H2O
–
–
100
100
100
100
100
120
60
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
60
70
100
100
0
2
Grinding, rt
Grinding, rt
Grinding, rt
Reflux
1 drop
2.5
2.5
3
–
1 drop
6
–
1 drop
2
MeOH
EtOH
EtOAc
THF
CH3CN
H2O
–
–
100
100
100
100
100
120
60
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
0
3
Reflux
–
60
80
100
100
2
Grinding, rt
Grinding, rt
Grinding, rt
1 drop
1 drop
1 drop
2.5
2.5
–
10
–
5

F
H. Mousavi et al.
Table 2. Comparison of the catalytic activity of prepared nanocom-
posites with their component parts
essential. It is very important to note that all of our efforts
for the reduction of aliphatic nitro compounds using the
current reduction systems failed (Table 3, entries 22 and 23).
A plausible mechanism for the reduction of aromatic nitro
compounds to arylamines with NaBH4 in the presence of nickel
boride-based nanocomposites is shown in Scheme 2.
NH2
NO2
Catalyst, NaBH4 (2.5 mmol)
Solvent-free, one drop H2O
Grinding, room temperature
Reusability of the Ni2B-Based Nanocomposites
The recovery and reusability of a catalyst is a very important
aspect in green catalytic processes. The recoverability and
reusability of the prepared nanocomposites were investigated
in this reduction reaction. After completion of the first reac-
tion, we added water (5 mL) to the reaction medium. Next,
the black solid was separated simply by filtration and
then further washed with water and ethanol and dried at
room temperature. After spectral analysis, it was found that the
black powder obtained was Ni2B. This means that the Lewis
acid part of the nanocomposites was removed during the
reaction process and/or during separation (after adding water).
In the next step, we grafted fresh Lewis acids (namely ZrCl4,
Cu2O, CuCl2, and FeCl3) on the recovered nickel boride. We
observed no significant change in the activity of the rebuilt
Ni2B-based nanocomposites during the recycling experiment
with fresh nitrobenzene under the optimized reaction
conditions.
Entry Catalyst
Time [min] Conversion [%]
1
Ni2B (0.2 mmol)
60
60
60
60
60
60
60
60
60
3
50
5
2
ZrCl4 (0.2 mmol)
3
Cu2O (0.2 mmol)
5
4
CuCl2 (0.2 mmol)
0
5
FeCl3 (0.2 mmol)
5
6
Ni2B (0.2 mmol) þ ZrCl4 (0.2 mmol)
Ni2B (0.2 mmol) þ Cu2O (0.2 mmol)
Ni2B (0.2 mmol) þ CuCl2 (0.2 mmol)
Ni2B (0.2 mmol) þ FeCl3 (0.2 mmol)
Ni2B@ZrCl4 (72 mg)
55
65
60
60
100
100
100
100
7
8
9
10
11
12
13
Ni2B@Cu2O (54 mg)
1
Ni2B@CuCl2 (52 mg)
2
Ni2B@FeCl3 (58 mg)
5
reflux. When the reaction was carried out with 2.5 mmol of
NaBH4 and one drop of water in the presence of Ni2B@ZrCl4
(72 mg) under solvent-free reaction conditions using a mech-
anochemical grinding technique (Table 1, entry 9), the best
result was achieved in a short time of 3 min. We repeated all the
optimization steps (mentioned above) in the presence of the
other new nanocomposites Ni2B@Cu2O, Ni2B@CuCl2, and
Ni2B@FeCl3. Interestingly, we found that all the four new
nanocomposites exhibited significant catalytic effects in the
reduction of nitrobenzene to aniline under solvent-free reac-
tion conditions at room temperature. It should also be men-
tioned that when the model reaction was attempted with Ni2B,
ZrCl4, Cu2O, CuCl2 alone, and also FeCl3 under the optimal
reaction conditions, the nitrobenzene reduction process was
very disappointing, in that after a fairly long time (60 min), the
reaction was not complete (Table 2, entries 1–5). Also, we
tested the model reaction using Ni2B nanoparticles along with
the aforementioned Lewis acids simultaneously as combined
catalytic systems (Table 2, entries 6–9). Unfortunately, these
two-component catalytic systems were also not suitable for the
reduction of nitrobenzene. Therefore, as shown in Table 2, our
prepared nanomaterials play a very important role in this
reduction reaction. In the next step, with the optimal reaction
conditions in hand, various types of aromatic nitro compounds
including some with both electron-withdrawing (EWD) and
electron-donating groups (EDG) were converted to the corre-
sponding arylamines in excellent yields (Table 3). Notably, in
some aromatic nitro compounds having acetyl or formyl sub-
stituents, reactions were typically complete, with reduction of
both nitro and carbonyl functional groups. Amide (Table 3,
entry 12) and dinitro- (Table 3, entry 19) groups and nitro-
phenyl hydrazine (Table 3, entry 20) or nitrophenyl carboxylic
acid (Table 3, entry 21) did not undergo any change in the
studied systems. It should be noted that no reduction reaction
takes place without wet reaction conditions. Therefore, the
presence of one drop of water inside the reaction medium is
Comparative Study
To show the value, efficiency, and capability of the present
green and expeditious protocols for the reduction of aromatic
nitro compounds to the corresponding arylamines, they were
compared with some previously reported methodologies.
Results are summarized in Table 4. It is worth noting that the
new protocols presented in the current paper are superior to
many of the others in terms of catalyst loading, reaction time,
cost-effectiveness, favourable yields of products, non-use of
solvent, use of solvent-free mechanochemical grinding tech-
nique, and so on.
Conclusions
A series of new nickel boride-based nanocomposites, namely
Ni2B@ZrCl4, Ni2B@Cu2O, Ni2B@CuCl2, and Ni2B@FeCl3,
were prepared using a simple operation and characterized by
FT-IR, XRD, SEM, and EDX. All the synthesized Ni2B-based
nanocomposites showed very satisfactory catalytic activity in
the reduction of aromatic nitro compounds to the corresponding
arylamines. The reaction occurs with NaBH4 as a reducing agent
under wet-solvent-free mechanochemical grinding. It is worthy
of note that the reduction protocols described have significant
advantages (especially from the standpoint of green chemistry
and industrial chemistry), including very short reaction times,
high yields of products, the use of nickel boride-based nano-
composites as very inexpensive new nanocatalysts, non-use of
toxic solvents, and the use of a wet-solvent-free mechano-
chemical grinding technique.
Supplementary Material
FT-IR, XRD, SEM, and EDX results of all Ni2B-based
nanocomposites along with FT-IR and SEM results of Ni2B
nanoparticles and also some selected FT-IR and H NMR
spectra of prepared amines are available on the Journal’s
website.

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Green Reduction of Nitroarenes to Arylamines
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Green Reduction of Nitroarenes to Arylamines
K
Ar
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Scheme 2. Plausible mechanism for the reduction of aromatic nitro
compounds to arylamines with NaBH4 in the presence of nickel boride-
based nanocomposites.
Conflict of interest
The authors declare no conflicts of interest.
(f) R. Ghorbani-Vaghei, S. Alavinia, Z. Merati, V. Izadkhah, Appl.
Organomet. Chem. 2018, 32, doi:10.1002/AOC.4127
(g) E. Colacino, A. Porcheddu, I. Halasz, C. Charnay, F. Delogu, R.
Guerra, J. Fullenwarth, Green Chem. 2018, 20, 2973. doi:10.1039/
C8GC01345D
Acknowledgement
We are thankful to the Research Council of Urmia University for the partial
support of this work.
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