Cobalt nanoparticles supported on ionic liquid-functionalized multiwall carbon nanotubes as an efficient and recyclable catalyst for Heck reaction

Article abstract of DOI:10.1002/aoc.3372

A novel and environmentally friendly cobalt nanoparticle catalyst supported on ionic liquid-functionalized multiwall carbon nanotubes was successfully prepared and evaluated as a heterogeneous catalyst for the Mizoroki-Heck reaction. Several reaction parameters, including type and amount of solvent and base, were evaluated. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity.

Full text of DOI:10.1002/aoc.3372

Full paper
Received: 27 June 2015
Accepted: 27 July 2015
Published online in Wiley Online Library: 13 September 2015
(wileyonlinelibrary.com) DOI 10.1002/aoc.3372
Cobalt nanoparticles supported on ionic liquid-
functionalized multiwall carbon nanotubes as
an efficient and recyclable catalyst for
Heck reaction
a,b
a
a,c
Abdol R. Hajipour *, Zahra Khorsandi and Hirbod Karimi
A novel and environmentally friendly cobalt nanoparticle catalyst supported on ionic liquid-functionalized multiwall carbon
nanotubes was successfully prepared and evaluated as a heterogeneous catalyst for the Mizoroki–Heck reaction. Several reaction
parameters, including type and amount of solvent and base, were evaluated. This nanocatalyst could also be recovered and
reused at least six times without any discernible decrease in its catalytic activity. Copyright © 2015 John Wiley & Sons, Ltd.
Additional supporting information may be found in the online version of this article at the publisher’s web site.
Keywords: cobalt nanoparticles; multiwall carbon nanotubes; Heck reaction; ionic liquid
often cause kinetic problems such as aggregation of metal particles
Introduction
[
23,40]
and reductions in catalytic activity.
The purpose of the stabi-
In the past decade, metal-catalyzed cross-coupling reactions have
lizer is to control the particle size and prevent agglomeration which
[41–44]
been considered extremely powerful synthetic tools for C–C bond
can be achieved by using ionic liquids (ILs) as stabilizers.
Even
[1–4]
formation.
Among the many different coupling protocols that
though the details of the stabilization mechanism have not been
clarified, it seems ILs create an electrostatic and steric barrier
have been previously reported, the palladium-catalyzed carbon–
carbon bond forming reaction between aryl halides and olefins in
the presence of a base (Heck reaction) is a powerful method for
[
45–47]
between the NPs which can overcome aggregation problems.
Carbon nanotubes (CNTs) are allotropes of carbon with a cylindrical
nanostructure exhibiting unique properties such as high mechani-
cal strength, tuneable porosity, high surface area, notable electronic
interactions with metal catalysts, mesoporous structure and
extraordinary stability in acid and basic media as well as at high
[4]
the synthesis of various organic molecules. It has not only been
[
5–11]
thoroughly studied in the laboratory,
but also many of the sig-
nificant uses and connected patents show its fundamental position
in the preparation of a broad array of products such as monomers,
pharmaceuticals and bioactive compounds, natural products,
sunscreen agents, herbicides and high-performance materials.
Hence, considerable efforts have been made to find new catalytic
[
48–50]
pressures and temperatures.
show novel properties as catalyst supports, especially in heteroge-
neous catalysis.
Owing to these properties, CNTs
[51–53]
The use of IL–CNT hybrids is thus one of the
[12–17]
systems and methodologies to improve this reaction.
Despite
most elegant and efficient ways to solve the problem of catalyst re-
[54–56]
the higher catalytic activities of homogeneous catalysts than their
heterogeneous counterparts, as with all homogeneous catalysts,
there are several problems such as separation, regeneration and
covery that minimizes the use of organic solvent.
We recently
reported the application of palladium complexes with quaternary
phosphonium cations immobilized covalently onto a solid support
[
18–20]
[57,58]
reuse of the expensive catalyst.
Moreover, The tradition cata-
in the Heck coupling reaction.
lysts for cross-coupling reactions are palladium complexes; the
application of palladium complexes has some limitations such as
With these considerations in mind, and as part of ongoing work
[
58–60]
towards the development of efficient green catalysts
with
[
21–23]
[61–63]
toxicity, cost, non-reusability and sensitively to air.
These
particular emphasis on the Heck reaction,
we report herein
problems can be largely overcome by carrying out the reactions
using heterogeneous-based catalysts, use of green solvents as reac-
tion solvents and/or using other transition metals which has
attracted much attention during recent years, for example, Ni, Cu,
* Correspondence to: Abdol R. Hajipour, Pharmaceutical Research Laboratory,
Department of Chemistry, Isfahan University of Technology, Isfahan 84156, IR
Iran. E-mail: haji@cc.iut.ac.ir
[24–30]
Co and Fe.
Cobalt-catalyzed couplings are of interest in or-
ganic synthesis, because cobalt is a non-toxic, inexpensive, widely
a Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan
University of Technology, Isfahan 84156, IR, Iran
[
31–33]
available and high-activity catalyst.
based catalysts have been reported for the Heck reaction.
Stabilized metallic nanoparticles (NPs) have been used as cata-
Recently, some cobalt-
[
34–36]
b Department of Pharmacology, University of Wisconsin, Medical School, 1300
University Avenue, Madison, WI 53706-1532, USA
[
37–39]
lysts and photocatalysts for many years.
The activity of these
materials is controlled by their size, crystal structure and the nature
of the stabilizer. However, having very active surface atoms can
c Young Researchers and Elite Club, Shahreza Branch, Islamic Azad University,
Shahreza, Iran
Appl. Organometal. Chem. 2015, 29, 805–808
Copyright © 2015 John Wiley & Sons, Ltd.

A. R. Hajipour et al.
anovel and unique catalyst that consists of an imidazolium ionic
liquid supported on multiwall carbon nanotubes (MWCNTs) based
on electrostatic bonding and cobalt NPs deposited on this surface
under mild conditions. This catalyst matrix contains carboxylated
MWCNTs, 1-butyl-3-methylimidazolium chloride, [bmim][Cl], and
cobalt NPs, which can act as a low-cost and efficient catalyst in
the Heck reaction (Scheme 1).
adsorption emission (ICP-OES) analyses indicate 55.3 wt% of Co is
deposited onto the Co-IL-MWCNT corresponding to 87.8% of the
Co used. The cobalt loading was 0.024 mmolg determined using
atomic absorption analysis.
ꢀ
1
X-ray diffraction (XRD) results for Co-IL-MWCNT are shown in Fig. S2.
All peaks can be indexed as Co by comparison with the JCPDS card file
[69,70]
no. 1-1255 demonstrating the structure of these Co(0) NPs.
No
other impurities including cobalt oxides or hydroxides are identified.
Fourier transform infrared (FT-IR) spectroscopy evidences the
structure of Co-IL-MWCNT. A strong sharp band with peak maxi-
Results and discussion
ꢀ
1
mum at 1641 cm corresponds to the C¼N bond. The broad peaks
ꢀ
1
Scanning electron microscopy (Fig. S1) was used to characterize
the morphologies of the cobalt NP catalyst supported on IL-
functionalized MWCNTs (Co-IL-MWCNT). As can be seen, the tubu-
lar structure of MWCNTs after fictionalization and anion-exchange
process remains almost intact. It is clear that small-sized Co NPs
between 2850 and 3300 cm , with peak maxima at 2850, 2950,
ꢀ
1
3100 and 3300 cm , are attributed to the aliphatic C–H stretching
bands and aromatic C–H stretching bands. The sharp band around
ꢀ
1
[65,71]
1060 cm corresponds to the C–N bonds (Fig. S3).
The thermal stability of MWCNTs, IL and Co-IL-MWCNT was inves-
tigated using thermogravimetric analysis (Fig. S4). The measure-
ments were carried out in the range 30–800°C with a ramp of
(small dots) present a moderately high density, non-ordered distri-
bution along the walls of the nanotubes. Also, transmission electron
microscopy (TEM) images of the Co-IL-MWCNT catalyst (Fig. 1)
clearly show round Co present at moderately high density and with
fairly even, non-ordered distribution along the walls and at the
ends of nanotubes. Very similar morphology observations have
ꢀ
1
10°Cmin in air. The catalyst sample decomposes in two major
[
65,69,72]
steps.
It is observed that adsorbed IL starts to degrade at a
lower temperature compared to neat IL, which may be due to
changes in the IL structure as a result of the interaction with CNTs
[
64–68]
[73]
been previously reported.
Inductively coupled plasma atomic
and the presence of Co NPs on CNT surface. These results indi-
cate the successful noncovalent and simple attachment of [bmim]
[Cl] and Co NPs onto the MWCNT surface.
The reactivity of the Co-IL-MWCNT catalyst was investigated in
the Heck cross-coupling reaction of iodobenzene and olefin. Base,
solvent and amount of catalyst were varied in the experiments.
The results show that these parameters are critical to the outcome
of the reaction (Table 1).
To get information on the optimal catalyst conditions, we carried
out in-depth investigations to determine the best solvent for this
transformation. Among the various solvents screened, such as
n-hexane, dioxane, tetrahydrofuran (THF) and toluene, the latter is
found to be the best solvent for this transformation. The nature of
the base is also crucial to the Heck reaction. Hence, several bases
Scheme 1. Synthesis of Co nanoparticles supported on imidazolium-
functionalized MWCNTs (Co-IL-MWCNT) in water.
a
Table 1. Optimization of reaction conditions
b
Entry
Solvent
THF
Base (equiv.) Catalyst 2 (mol% Co) Yield (%)
1
2
3
4
5
6
7
6
7
8
9
NaHSO
NaHSO
NaHSO
4
4
4
4
4
4
4
(1.5)
(1.5)
(1.5)
(1.5)
(1.5)
(2)
5
5
5
5
5
5
5
5
5
5
5
7
37
5
Dioxane
n-Hexane
46
52
77
81
87
62
59
48
44
83
n-Heptane NaHSO
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
n-Hexane
NaHSO
NaHSO
NaHSO
(3)
Na CO
2 3
(1.5)
K CO (1.5)
2 3
NaOH (1.5)
KOH (1.5)
10
4
NaHSO (1.5)
a
The reaction was carried out with iodobenzene (1.0 mmol), methyl
acrylate (1.5 mmol) and base at 100°C or reflux condition.
b
Isolated pure products.
Figure 1. TEM images of Co-IL-MWCNT.
wileyonlinelibrary.com/journal/aoc
Copyright © 2015 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2015, 29, 805–808

Cobalt–carbon nanotube catalyst for Heck reaction
a
were tested for this reaction: NaHSO
4
is determined to be the most
Table 3. Recyclability of Co-IL-MWCNT
effective (Table 1, entry 5). An amount of 5 mol% Co results in the
best conversion in 3 h at 100°C (Table 1, entry 5). The extent of
Co leaching after the reaction was determined using ICP-OES, and
no leaching of Co is detected.
b
b
Run
Yield (%)
Run
Yield (%)
1
2
3
87
85
86
4
5
6
82
76
77
These optimized reaction conditions were applied in the Heck re-
action for a variety of aryl halides with various olefins. The results
are summarized in Table 2. The results show that aryl halides with
electron-withdrawing groups react with olefins faster with shorter
reaction times than those with electron-donating substituents. Also
the results in Table 2 clearly show that the coupling reactions with
methyl acrylate (MA) as the olefin are faster than those with methyl
methacrylate (MMA) and styrene. In all of the reactions, only the
E-isomers are produced. All of the products are known and were
characterized by comparing their physical properties such as
a
The reaction was carried out with iodobenzene (1.0 mmol), methyl
acrylate (1.5 mmol) and NaHSO (3 mmol) in toluene in the
presence of 5 mol% Co of Co-IL-MWCNT (2) at 100°C.
Isolated yield.
4
b
Conclusions
1
13
FT-IR, H NMR and C NMR spectra with those reported in the
In summary, we have prepared Co NPs immobilized on imidazolium
ionic liquid-functionalized MWCNTs (Co-IL-MWCNT) which can be
used as an environmentally friendly and economical catalyst for
the Heck coupling reaction. This coupling reaction can proceed
without the need for an expensive palladium catalyst and toxic
ligands in a markedly short reaction time.
[57,58,61–63]
literature.
The reusability of the catalyst was tested using iodobenzene
and MA as substrates (Table 3). After each run, the catalyst was
recovered by centrifugation, followed by washing with acetone
(2 × 3 ml). The activity of the catalyst remains almost unchanged
after being reused six times, indicating that the catalyst is not only
active enough for the Heck reaction, but also very stable.
The catalytic activity of Co-IL-MWCNT was compared with other
Experimental
[
34,74]
Co NPs that have been reported previously.
It is found that
General
the reaction time is much shorter in the presence of Co-IL-MWCNT
than Co NPs.
All chemical reagents were purchased from Merck and were used
without purification. All products were characterized in terms of
1
their physical properties. H NMR spectra were recorded at
13
4
00 MHz and C NMR spectra were recorded at 100 MHz (Bruker)
Table 2. Scope of aryl halide in Co-IL-MWCNT (2)-catalyzed coupling
a
with CDCl or DMSO-d as solvent. Chemical shifts are reported in
3
6
reaction with olefins
ppm using tetramethysilane as an internal standard. FT-IR spectra
were obtained using KBr pellets with a JASCO 680-Plus spectropho-
tometer. Also, we used GC (Beifin 3420 gas chromatograph
equipped with a Varian CP SIL 5CB column: 30 m, 0.32 mm,
0.25 mm) for investigation of reaction conversions.
b
Entry
X
R
Olefin
MA
Time (h)
Yield (%)
Preparation of Co-IL-MWCNT (2)
1
2
3
4
5
6
7
8
9
I
I
I
H
3
87
90
58
53
79
60
58
55
46
74
81
77
63
68
70
69
57
62
66
Purified carboxylic oxidized CNTs (0.500 g) were mixed with a solu-
tion of sodium hydroxide (25 ml, 0.05 M) for 24 h at room temper-
ature in order to produce the sodium salt of the acidified
nanotubes. The solid was filtered and washed with water until the
pH reached 7. The resulting solid was treated with an excess of
4-NO
2
MA
3
4-OMe
H
MA
3
Br
Br
Br
Br
Br
Br
I
MA
8
4-NO
2
MA
8
4-Cl
2-Cl
4-OMe
4-Me
H
MA
8
[
bmim][Cl] (0.300 g) at 55°C for 24 h, followed by a filtration step
and then washed with water to afford IL-MWCNT. Subsequently,
.0 ml of aqueous Na CoCl (0.04 g) was added to 10 ml of an aque-
MA
8
MA
8
1
2
4
MA
8
ous suspension of as-prepared IL-MWCNT (0.250 g) and 10 ml of an
10
11
12
13
14
15
16
17
18
19
Styrene
Styrene
Styrene
Styrene
Styrene
Styrene
Styrene
Styrene
MMA
MMA
16
16
16
16
16
16
16
16
16
16
aqueous solution of NaBH (0.1 g). The resulting mixture was stirred
4
I
4-NO
2
for 6 h at room temperature. The resultant products were isolated
I
4-OMe
H
by centrifugation, washed and dried under vacuum for 24 h at
Br
Br
Br
Br
Br
I
[75,76]
50°C to afford Co-IL-MWCNT in 75% yield.
4-NO
4-Cl
2-Cl
4-Me
H
2
General procedure for Heck reaction
Under air atmosphere, NaHSO (3 equiv.), olefin (1.5 mmol), aryl ha-
4
lide (1 mmol), catalyst 2 (5 mol% Co) and toluene (5 ml) were added
into a round-bottomed flask equipped with a condenser and mag-
netic stirrer at 100°C. The progress of the reaction was monitored
using GC. After completion of the reaction, the reaction mixture
was cooled to room temperature, and the product was extracted
with n-hexane (3 × 5 ml). The catalyst was separated by centrifuga-
tion, and washed with acetone. After drying, the catalyst was
I
4-OMe
a
The reaction was carried out with halobenzene (1.0 mmol), olefin
1.5 mmol) and NaHSO (3 mmol) in toluene in the presence of 5
mol% Co of Co-IL-MWCNT (2) at 100°C.
(
4
b
Isolated pure products.
Appl. Organometal. Chem. 2015, 29, 805–808
Copyright © 2015 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/aoc

A. R. Hajipour et al.
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The authors thank Isfahan University of Technology (IUT), IR Iran.
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