Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efficient and Recyclable Heterogeneous Catalyst for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction in Water

Article abstract of DOI:10.1007/s10562-021-03637-1

An efficient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltetracarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM. Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst could be applied as an efficient and reusable heterogeneous catalyst for above two reactions. Graphical Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s10562-021-03637-1

Catalysis Letters
https://doi.org/10.1007/s10562-021-03637-1
Palladium Immobilized on a Polyimide Covalent Organic
Framework: An Efcient and Recyclable Heterogeneous Catalyst
for the Suzuki–Miyaura Coupling Reaction and Nitroarene Reduction
in Water
Zhenhua Dong1 · Hongguo Pan1 · Pengwei Gao1 · Yongmei Xiao1 · Lulu Fan1 · Jing Chen1 · Wentao Wang2
Received: 28 February 2021 / Accepted: 14 April 2021
© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2021
Abstract
An efcient and recyclable Pd nano-catalyst was developed via immobilization of Pd nanoparticles on polyimide linked
covalent organic frameworks (PCOFs) that was facilely prepared through condensation of melamine and 3,3′,4,4′-biphenyltet-
racarboxylic dianhydride. The Pd nanoparticles (Pd NPs) catalyst was thoroughly characterized by FT-IR, XRD, SEM, TEM.
Furthermore, the catalytic activity of Pd NPs catalyst was evaluated by Suzuki–Miyaura coupling reaction and nitroarene
reduction in water, respectively. The excellent yields of corresponding products revealing revealed that the Pd NPs catalyst
could be applied as an efcient and reusable heterogeneous catalyst for above two reactions.
Graphical Abstract
N
N
I
B(OH)2
O
O
NH2
Ar1
+
Ar2
N
N
N
Ar
O
O
O
O
N
N
N
O
N
N
Pd
O
O
N
N
N
N
Pd
O
Pd
N
O
O
O
O
O
O
N
N
Pd
O
Pd
O
N
N
N
N
N
N
N
N
Pd
O
N
O
O
O
N
N
O
O
N
N
Ar1
NO2
Ar2
Ar
Keywords Covalent organic framework · Pd nanoparticles · Porous materials · Suzuki–Miyaura cross coupling · Reduction
of nitroarenes
1 Introduction
As we know, the efcient catalytic process not only refers
to produce the target products in high yields via applying
high reactive catalyst, but also require the reaction procedure
and work-up to easily handle. The heterogeneous catalysis
can meet the requirement of such efcient catalytic process
because the heterogeneous catalyst can be reused and easily
separated from reaction solution, compared with homoge-
neous catalysis [1–3]. Nano-catalysis, as an emerging fron-
tier in heterogeneous catalysis, has received considerable
attention in recent years [4, 5]. Typically, the nano-catalysis
* Zhenhua Dong
zhdong@haut.edu.cn
* Wentao Wang
wentaowang@dicp.ac.cn
1
College of Chemistry and Chemical Engineering,
Henan University of Technology, Lianhua Street 100,
Zhengzhou 450001, China
2
Dalian Institute of Chemical Physics, Chinese Academy
of Sciences, Zhongshan Road 457, Dalian 116023, China
Vol.:(0123456789)
1 3

Z. Dong et al.
applied the noble metal nanoparticles have played quite
important role in organic synthesis, and shown a wide range
of applications for synthesis of diverse fne chemicals and
bioactive compounds [6–11]. The excellent catalytic reac-
tivity of nanoparticles (NPs extremely depend on the metal
size, shape and the number of atoms on the NPs surface,
because the catalytic process mainly takes place on the metal
surface, and the more surface explored by metal could pro-
duce more catalytic centers [12–14]. Therefore, it is highly
desirable to decreasing metal particle size for improving
metal catalytic reactivity. However, a challenge has to be
considered is that ultrafne NPs are easy to aggregate to form
greater aggregations owing to their high surface energy,
greater aggregations result in the loss of catalytic activity
gradually. As a result, various supported materials were
explored to immobilize the ultrafne NPs, in order to avoid
the aggregation of NPs and obtain the stable nano-catalyst.
So far, a variety of supported material have been developed,
such as metal oxides [15], polymers [16, 17], silica [18] and
so on. However, the preparation of stable ultrafne metal NPs
still remains a challenging task.
catalytic systems were only ft for the sole Suzuki–Miyaura
coupling reaction or nitroarenes reduction, could not be
applied in both reactions. The development of COFs sup-
ported Pd NPs that could catalyze both Suzuki–Miyaura
coupling reaction and nitroarenes reduction would highly
signifcant and desirable. Herein, we report an efcient cata-
lytic system to achieve the possibility of supported Pd NPs
can catalyze both Suzuki–Miyaura coupling reaction and
nitroarenes reduction. Firstly, an ecofriendly and economi-
cal method were explored to synthesize a polyimide linked
covalent organic frameworks (PCOFs) [38–40] that served
as a template for the preparation of nano Pd heterogeneous
catalyst. Then the stability and reactivity of Pd@PCOFs cat-
alyst were inspected by Suzuki–Miyaura coupling reaction
and nitroarene reduction, and the corresponding products
of two reactions were all gained in excellent yields. Com-
paring with previous reports, the present protocol have the
bellow advantages: (1) Polyimide linked COFs were easy to
synthesize and the Pd@PCOFs were highly dispersed with
low Pd loading. (2) The Suzuki–Miyaura coupling reaction
could proceed efciently with very low Pd loading (up to
0.004 mol% Pd). The catalyst loading is dramatically lower
than previous reports. (3) The two reactions both could
proceed in aqueous medium under air. (4) The Pd@PCOFs
could be recycled with high reactivity.
In the past decade, covalent organic frameworks (COFs)
have been developed as a new generation of emerging
organic porous polymers formed between C, B, N, O or S
by strong covalent bonds [19–22]. They have been applied in
gas storage and purifcation [23], drug delivery [24], cataly-
sis [25], energy storage [26] and so on. Recently, the COFs
have been applied as outstanding hosts to support metal NPs
[27]. Comparing with traditional supported materials, the
COFs possess the following advantages: (1) The COFs have
defnite pores in their structures, and the metal NPs can grow
in the pore channels. The size and shape of metal NPs can be
controlled and confned. (2) The aggregation of metal NPs
can be minimized because every pore channel is isolated in
COFs. (3) The COFs have diverse functional groups that can
be coordinated with diferent metals. (4) In general, COFs
are insoluble in most solvents. Thus, it will be stable under
various reaction conditions and can be easily separated and
recycled.
2 Results and Discussion
The polyimide based covalent organic frameworks (PCOFs)
was synthesized by the condensation reaction of melamine
and 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA)
as depicted in Scheme 1. The 1:1 molar ratio of melamine
and BPDA were initially mixed and ground uniformly. Then
the mixture was calcined in an alumina crucible by mufe
furnace at 325 °C for 4 h. After that, the resultant solid was
washed with water to give pure PCOFs in high yield. Com-
paring with the preparation of imine linked PCOFs, this syn-
thetic protocol was rather simple, easier to handle and more
environmentally-friendly. Furthermore, the polymerization
had no need to use sealed reaction tube and no hazardous
waste was produced as well. In addition, the PCOFs was
stable in air and insoluble in commercially available sol-
vents, including water, DCM, DMF, Toluene, THF, acetone,
DMSO, etc. Finally, the structure of PCOFs was confrmed
by FT-IR (Fourier transform infrared spectroscopy), SEM
(scanning electron microscopy), XRD (X-ray difraction
analysis), TGA (thermal gravimetric analysis). and BET
(Brunauer–Emmett–Teller).
Suzuki–Miyaura coupling reaction, as a Nobel reaction,
has been considered as one of the most efcient methods
for the construction of C–C bonds [28–32]. On the other
hand, aryl amine is one of most important intermediates in
the pharmaceutical and synthesis [33–35]. Although several
methods have been developed to synthesize the aryl amines,
the reduction of nitroarenes is still one of the most cost-
efcient methodologies [36, 37]. Hence, the development
of new and more efcient catalytic system is highly desir-
able for Suzuki–Miyaura coupling reaction and nitroarenes
reduction. The COFs supported metal NPs, such as Pd NPs,
have exhibited excellent catalytic activities in C–C coupling
reaction and nitroarenes reduction, and achieved much atten-
tion in the heterogeneous catalysis. However, the reported
The FT-IR spectroscopy was used to characterize the
PCOFs as shown in Fig. 1. The disappearance of band at
1844 cm−1 and 1775 cm−1 indicated that the starting anhy-
dride monomer BPDA had consumed completely after the
1 3

Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efcient and Recyclable…
Scheme 1 Preparation of
N
N
O
O
PCOFs and Pd@ PCOFs
N
N
N
O
O
O
O
N
O
N
N
O
N
O
N
N
O
O
O
N
N
N
N
O
O
O
O
O
O
325 o
C
NH2
N
N
O
O
O
O
N
N
H2N
N
NH2
N
N
N
N
O
O
N
N
N
N
O
O
O
O
N
N
N
O
O
N
N
1) Pd(OAc)2
2) NaBH4
N
N
O
O
N
N
N
O
O
O
O
N
N
N
N
Pd
O
O
N
N
N
N
Pd
O
Pd
N
N
O
O
O
O
O
O
O
N
N
N
Pd
O
Pd
O
N
N
N
N
N
N
N
Pd
O
N
O
O
O
N
N
O
O
N
N
reaction (Blue line). While the absorptions at 1759 cm−1 and
1711 cm−1 shown in spectrum of PCOFs (red line) demon-
strated the existence of C=O groups, indicating the forma-
tion of polyimide[39].
The microstructure of PCOFs was characterized by
SEM and the images displayed that PCOFs template was
porous and resembling spongy (Fig. 2). The cross-linked
polymers with crystalline structures could be shown direct
visualization. As shown in Fig. S1 (Supporting Informa-
tion), the N2 adsorption/ desorption isotherm was measured
at 77 K, giving the result of surface area and pore diameter
as 36.36 m2 g−1.
The immobilization of Pd NPs on PCOFs was subse-
quently performed. The Pd precursor was frstly deposited
into the PCOFs material by adding Pd(OAc)2 to a suspension
of PCOFs with stirring. Then the mixture was reduced by
NaBH4. After that, the resulted mixture was fltered and the
solid was washed and dried under vacuum to provide target
Fig. 1 FT-IR spectra of BPDA and PCOFs
1 3

Z. Dong et al.
Fig. 3 XRD images of PCOFs and Pd@ PCOFs
in the PCOFs. The particle size of Pd@ PCOFs was in the
3–5 nm range and the shapes were spherical (Fig. 4).
Subsequently, the catalytic activity of Pd@PCOFs was
evaluated against the Suzuki–Miyaura coupling reaction by
using iodine benzene (1a) and phenyl boronic acid (2a) as
model substrates. The reaction parameters such as catalyst
loading, base, solvent and temperature were examined to
optimized the reaction conditions and the results were sum-
marized in Table 1. When the reaction was carried out using
10 mg Pd@PCOFs as heterogeneous catalyst and K2CO3 as
base in DMSO at 110 ℃ for 6 h, the coupling product biphe-
nyl (3a) was obtained in excellent yield (Table 1, entry 1).
While, the reaction could not produce neither in the absence
of Pd@PCOFs catalyst nor in the presence of PCOFs alone
(Table 1, entries 2 and 3). These results revealed that the key
role of Pd nanoparticles as catalysts in the Suzuki–Miyaura
coupling reaction. The optimizations of base were then
checked by using Cs2CO3 and tBuOK respectively. Unfor-
tunately, no improvement of yield was achieved (Table 1,
entries 4 and 5). Meanwhile, the reaction did not occur
when the base was absent (Table 1, entry 6). A variety of
solvents, such as DMF, toluene and H2O were next investi-
gated (Table 1, entries 7–9). To our delight, the quantitative
yield of 3a was obtained when H2O was used as solvent at
80 ℃ (Table 1, entry 9). However, the reduction of tempera-
ture resulted in the decreasing yield dramatically (Table 1,
entries 10 and 11). Notably, the catalyst loading could be
diminished to 0.004 mol% palladium loading (using 5 mg
Pd@PCOFs) without any loss of the yield of 3a (Table 1,
entry 12). The comparison between previous reported works
and the present work for Suzuki–Miyaura coupling reaction
has been summarized in Table S1 in supporting information
accompanying this paper.
Fig. 2 The SEM images of PCOFs
Pd@ PCOFs nano-catalyst for further use. The Pd content in
the Pd@ PCOFs was determined to be 0.42 wt % by induc-
tively coupled plasma (ICP) analysis. The low Pd loading
indicated that the Pd NPs might deposit on the surface of
PCOFs rather than encapsulate inside the pore channels.
The powder XRD analysis provided the structural regu-
larity and crystalline nature of PCOFs and Pd@ PCOFs as
shown in Fig. 3. The relatively strong difraction peaks at
2θ=14.14 and 26.86° of PCOFs (blue line) exhibited that
the crystallinities of PCOFs were acceptable. However, no
signifcant changes were observed from the XRD of Pd@
PCOFs, indicating that the loading amount of Pd NPs was
relatively low. This result was consistent with the data
of ICP-AES. In addition, the stability of the catalyst was
explored by thermogravimetric analysis (TGA). As shown
in Fig. S2 (Supporting Information), The result displayed
excellent thermal stability of Pd@PCOFs with thermal
decomposition temperatures exceeding 457.2 °C.
The shape and morphology of Pd NPs supported on
PCOFs was determined by TEM analysis. The TEM images
suggested that Pd nanoparticles were uniformly distributed
With the optimized reaction conditions in hand, the cata-
lytic applicability of Pd@PCOFs was explored subsequently
for various aryl iodides and arylboronic acids in water. As
1 3

Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efcient and Recyclable…
Fig. 4 The TEM images of
Pd@PCOFs
shown in Table 2, a series of aryl iodides with electron-with-
drawing and electron-donating groups proceeded smoothly
to provide the corresponding products in excellent yields
(Table 2, entries 2–6). Meanwhile, various substituted
boronic acid partners were also tolerated well for the reac-
tion to generate the products 3d to 3e with 95–99% yields
(Table 2, entries 7–9).
collected in Table 3. A series of substituted nitroarenes were
reacted very well to give the corresponding primary amines
in high to excellent yields. For instance, the nitroarenes with
substituted CH3, Cl, Br, I, MeO groups, were all tolerated
well in this catalytic system (Table 3, entries 2–10). There
had no obvious diference on the reactivity for electron-
donating and withdrawing groups. The 4-Cl-substituted ani-
line (5e) and 2-Cl-substituted aniline (5 g) were produced in
99% and 82% yield respectively, which suggested that the
steric hindrance might has slight efect in this transforma-
tion (Table 3, entries 5 and 7). In addition, this methodology
could be applied to the reduction of aromatic heterocyclic
compounds as well. When 2-chloro-3-nitropyridine (4 k)
were introduced in this reaction, the corresponding product
was obtained in 99% isolated yields, respectively. In all cases
of Tables 1, 2 and 3, the isolated yields were calculated after
fash column chromatography. The purity of all products was
determined by thin layer chromatography (TLC).
Aromatic primary amines were widely used as impor-
tant organic intermediates in the chemical industry for the
production of pharmaceuticals, agrochemicals, polymers,
and dyes. The reduction of nitroarenes has been utilized
as a quite efective method for the synthesis of aromatic
primary amines. For further exploring the utility of Pd@
PCOFs as heterogeneous nano-catalyst, we assessed the pos-
sibility of synthesizing aromatic primary amines by Pd@
PCOFs catalyzed reduction of nitroarenes. When the reac-
tion was performed with 3 equivalent of NaBH4 as reductive
reagent and water as solvent at room temperature, aniline
product (5a) was obtained in 99% yield by using 10 mg Pd@
PCOFs (0.04 mol% catalyst loading) in 24 h. With this opti-
mized reaction conditions, various nitroarenes were further
evaluated to explore the substrate scope. The results were
The recyclability of Pd@PCOFs was further investigated
using Suzuki–Miyaura coupling reaction and reduction of
nitroarenes. The catalyst was separated by centrifugation
from the reaction mixture. The recovered catalyst was
1 3

Z. Dong et al.
Table 1 Optimization of reaction conditions of Suzuki reactiona
Entry
Catalyst
Base
Solvent
Temperature
Yieldb (%)
1
2
3
4
5
6
7
8
Pd@PCOFs
–
PCOFs
K2CO3
K2CO3
K2CO3
Cs2CO3
tBuOK
–
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
DMSO
DMSO
DMSO
DMSO
DMSO
Water
DMF
Toluene
Water
110
110
110
110
110
80
110
110
80
98
0
0
Pd@PCOFs
Pd@PCOFs
Pd@PCOFs
Pd@PCOFs
Pd@PCOFs
Pd@PCOFs
Pd@PCOFs
Pd@PCOFs
Pd@PCOFs
96
93
0
96
90
99
81
63
99
9
10
11
12c
Water
Water
Water
60
40
80
aIodobenzene (5 mmol, 1020.1 mg), phenyl boronic acid (7.5 mmol, 914.5 mg), base (10 mmol), Pd@PCOFs (Pd 0.42 wt%) 10 mg, solvent
(5.0 mL) for 6 h. bIsolated yield. cUsing 5 mg Pd@PCOFs
Table 2 Substrate scope of the Pd@PCOFs catalyzed Suzuki–Miyaura coupling reactiona
Entry
Ar1
Ar2
Product (3)
Yield(%)b
1
2
3
4
5
6
7
8
9
Ph
Ph
Ph
Ph
Ph
Ph
Ph
3a
3b
3c
3d
3e
3f
3d
3 g
3e
99
94
97
99
93
99
99
98
95
4-Cl-C6H4
3-Cl-C6H4
4-MeO-C6H4
3-MeO-C6H4
4-CH3CO–C6H4
Ph
4-MeO-C6H4
3,4-(MeO)2-C6H4
3-MeO-C6H4
Ph
Ph
aReaction conditions: aryl iodines 1 (5 mmol), arylboronic acids 2 (7.5 mmol), K2CO3 (10 mmol), Pd@PCOFs (5 mg), water (5 mL) at 80 °C for
6 h. aIsolated yields
carefully washed by ethanol, then dried and reused for next
reactions without further purifcation. The reaction of iodo-
benzene with phenylboronic acid was initially conducted
using 5 mg Pd@PCOFs catalyst under the optimized reac-
tion conditions. The results were summarized in Fig. 5. The
reaction outcomes indicated that the Pd@PCOFs catalyst
could be used two times without obvious loss of catalytic
activity. However, a slight loss in catalytic activity was
observed in the third run. In addition, the recyclability of
Pd@PCOFs was also tested for the reduction of nitroarene.
The results demonstrated that Pd@PCOFs catalyst could
also be used twice with the product retaining in 99% yield
1 3

Palladium Immobilized on a Polyimide Covalent Organic Framework: An Efcient and Recyclable…
Table 3 The Pd@PCOFs catalyzed reduction of nitroarenesa
Entry
ArNO2 (4)
Product (5)
Yield (%)b
1
2
3
4
5
6
7
8
PhNO2
5a
5b
5c
5d
5e
5f
5 g
5 h
5i
99
99
99
99
99
85
82
98
99
88
99
4-CH3-C6H4NO2
3-CH3-C6H4NO2
2-CH3-C6H4NO2
4-Cl-C6H4NO2
3-Cl-C6H4NO2
2-Cl-C6H4NO2
4-I-C6H4NO2
9
10
11
4-Br-C6H4NO2
2-MeO-C6H4NO2
5j
5 k
aReaction conditions: nitroarenes 4 (1 mmol), NaBH4 (3 mmol), Pd@PCOFs (0.04 mol% loading, 10 mg), room temperature, 2 mL water as sol-
vent, 24 h. bIsolated yield
5 mg
10 mg
B(OH)2
I
Pd@PCOFs
Pd@PCOFs
+
+
NaBH4
NO2
NH2
K2CO3, water
80 oC, 6h
water, r. t.
24h
3a
2a
1a
4a
5a
Fig. 6 The recyclability of Pd@PCOFs in the reduction of nitroarene
Fig. 5 The recyclability of Pd@PCOFs in the reaction of iodoben-
zene with phenylboronic acid
catalyst reactivity has diminished slightly. The leaching
of the catalyst was investigated. The ICP-AES analysis of
the frst recycled fltrate showed that trace amounts of Pd
(about 0.01% Pd) were leached into the solution. The results
revealed that the Pd maybe incorporated on the surfaces of
(Fig. 6). However, the yield of target product decreased
to 85% after two recycle use of Pd@PCOFs, showing the
1 3

Z. Dong et al.
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organic framework was synthesized by the solid-state ther-
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quently, highly dispersed Pd nanoparticles were successfully
immobilized on PCOFs and its catalytic performance was
evaluated for the Suzuki–Miyaura coupling reaction and ef-
cient reduction of aromatic nitro compounds. The reaction
conditions were environmentally favorable with excellent
yields. For electronically and structurally varied aryl halides,
arylboronic acids and nitroarenes, the Pd@PCOFs catalyst
works efectively to give good to excellent yield of the cor-
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Acknowledgements The authors are grateful to the Doctor Fund of
Henan University of Technology (No. 2015BS013) and The Colleges
and Universities Key Research Program Foundation of Henan Prov-
ince (No. 20A150014). The Project was also Supported by State Key
Laboratory of Materials Processing and Die & Mould Technology,
Huazhong University of Science and Technology (P2019-004)
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