Palladium catalyst immobilized on functionalized microporous organic polymers for C-C coupling reactions

Article abstract of DOI:10.1039/c9ra07303e

Two microporous organic polymer immobilized palladium (MOP-Pd) catalysts were prepared from benzene and 1,10-phenanthroline by Scholl coupling reaction and Friedel-Crafts reaction, respectively. The structure and composition of the catalyst were characterized by FT-IR, TGA, N₂ sorption, SEM, TEM, ICP-AES and XPS. MOP-Pd catalysts were found to possess high specific surface areas, large pore volume and low skeletal bone density. Moreover, the immobilized catalyst also had advantages, such as readily available raw materials, chemical and thermal stability, and low synthetic cost. The Pd catalyst is an effective heterogeneous catalyst for carbon-carbon (C-C) coupling reactions, such as the Heck reaction and Suzuki-Miyaura reaction, affording good to high yields. In these reactions, the catalyst was easily recovered and reused five times without significant activity loss.

Full text of DOI:10.1039/c9ra07303e

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Palladium catalyst immobilized on functionalized
microporous organic polymers for C–C coupling
reactions†
Cite this: RSC Adv., 2019, 9, 34595
*
Wei Xu,‡ Cijie Liu,‡ Dexuan Xiang,
Qionglin Luo, You Shu, Hongwei Lin,
*
Yangjian Hu, Zaixing Zhang and Yuejun Ouyang
Two microporous organic polymer immobilized palladium (MOP-Pd) catalysts were prepared from
benzene and 1,10-phenanthroline by Scholl coupling reaction and Friedel–Crafts reaction, respectively.
The structure and composition of the catalyst were characterized by FT-IR, TGA, N2 sorption, SEM, TEM,
ICP-AES and XPS. MOP-Pd catalysts were found to possess high specific surface areas, large pore
volume and low skeletal bone density. Moreover, the immobilized catalyst also had advantages, such as
readily available raw materials, chemical and thermal stability, and low synthetic cost. The Pd catalyst is
an effective heterogeneous catalyst for carbon–carbon (C–C) coupling reactions, such as the Heck
reaction and Suzuki–Miyaura reaction, affording good to high yields. In these reactions, the catalyst was
easily recovered and reused five times without significant activity loss.
Received 11th September 2019
Accepted 20th October 2019
DOI: 10.1039/c9ra07303e
rsc.li/rsc-advances
Carbon–carbon (C–C) coupling reactions have become one of reactivity, stability, easy separation, purication and recycla-
the most versatile and utilized reactions for the selective bility.14 Many active heterogeneous palladium catalysts have
construction of C–C bonds for the formation of functionalised been developed and widely applied in the C–C coupling reac-
aromatics,1 natural products,2 pharmaceuticals,3 polymers4 and tions.15 Palladium has been immobilized on various solid sup-
advanced materials.5 Many transition metals have been used as porting materials, such as zeolite,16 silica,17 metal organic
catalysts in these reactions, aided by a great variety of ligands frameworks,18 and functionalized graphene oxide.19 However,
ranging from simple, commercial phosphines to complex a substantial decrease in activity and selectivity of the hetero-
custom-made molecules.6 Among these transition metals, geneous palladium catalysts is frequently observed because of
palladium plays a signicant role in various cross-coupling their long diffusion pathway to catalytic sites and the difference
reactions, such as Suzuki,7 Heck,8 Sonogashira,9 Stille,10 and of electron density on active sites. To address these problems,
Ullmann coupling reactions,11 due to their strong electrical and materials with larger interface and more active site are
chemical properties.12 Over the past decades, various homoge- employed to support palladium as heterogeneous catalysts,
neous catalytic systems have been developed for organic such as palladium immobilized on hyper-crosslinked polymers
transformations,13 which oen progress smoothly under the were high activity in Suzuki–Miyaura coupling reaction.20
inert atmosphere in organic solvents, for example, toluene or
Microporous organic polymers (MOPs) consists of purely
tetrahydrofuran in the presence of soluble palladium complexes organic elements have recently emerged as versatile platforms
as catalysts. However, most homogeneous palladium catalysts for heterogeneous catalysts thanks to their unique properties,
suffer from drawbacks such as high-cost of phosphine ligands, including superior chemical, thermal and hydrothermal
use of various additives, difficult separation, metal leaching, stability, synthetic diversity, low skeletal density and high
recovery, recyclability, and the toxicity of phosphine ligands.
surface area.20,21 More importantly, the bottom–up approach of
Heterogeneous catalysis have attracted increasing attention MOPs provides an opportunity for the design of polymer
as they have been proven to be useful for different organic frameworks with a range of functionalities into the porous
reactions owning to their unique properties, such as high structure to use as catalysts or ligands.22 Recently, Kaskel re-
ported the incorporation of a thermally fragile imidazolium
moiety into MOPs resulted in a heterogeneous organocatalyst
active in carbene-catalyzed Umpolung reaction.23 Wang
Hunan Engineering Laboratory for Preparation Technology of Polyvinyl Alcohol (PVA)
Fiber Material, Institute of Organic Synthesis, Huaihua University, Huaihua 418000,
designed photocatalysts with microporous via the copolymeri-
China. E-mail: dexuanxiang@126.com; oyyj0816@163.com
zation from pyrene and dibenzothiophene-S,S-dioxide building
† Electronic supplementary information (ESI) available: Experimental details,
blocks and tested the effect of the photocatalytic hydrogen
evolution.24 Xu described the synthesis of microporous with N-
spectral characterization data and supplementary gures. See DOI:
10.1039/c9ra07303e
‡ Wei Xu and Cijie Liu contributed equally to this work.
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heterocyclic carbenes by an external cross-linking reaction and
applied it in Suzuki reaction.25 Zhou demonstrated for the rst
time that the microporous structure has a positive effect on
controlling selectivities in the hydrosilylation of alkynes.26
Recently, we also reported three pyridine-functionalized N-
heterocyclic carbene–palladium complexes and its application
in Suzuki–Miyaura coupling reactions.27
1,10-phenanthroline is an ideal candidate of ligands due to
its structural features such as two N-atom placed in juxta
position to provide binding sites for metal cations.28 To utilize
the unique structure feature, we employed it in the construction
of MOPs via Scholl and Friedel–Cras reaction, respectively.
Therefore, this paper presents our recent studies on the
synthesis of two heterogeneous palladium catalysts supported
on MOPs through a simple and low-cost procedure. These
catalysts displayed remarkable catalytic activity in C–C coupling
reactions, including Suzuki–Miyaura reaction and Heck
coupling reaction. The properties of simple preparation, wide
application of this catalyst and good performance in C–C
coupling reactions and adaptability with various substrates
make it perfect catalytic option for C–C coupling reactions.
The microporous network with 1,10-phenanthroline func-
tional groups and incorporation of Pd metal were conrmed by
Fourier transform infrared (FT-IR) spectroscopy. The FT-IR
spectra of MOPs and MOPs-Pd (Fig. 1) displayed a series of
bands around 2800–3100 cmꢀ1, which were assigned to the C–H
stretching band and in-of-plane bending vibrations of the aryl
rings. The bands around 1550–1750 cmꢀ1 were attributed to the
–C]N- stretching band. The bands around 1400–1450 and 850–
700 cmꢀ1 were corresponded to the benzene and 1,10-phenan-
throline skeletal stretching and the C–H out-of-plane bending
vibrations of the aryl rings, respectively. The bond around
1495 cmꢀ1 in MOPs-I and MOPs-Pd-I is assigned to in-of-plane
bending vibrations of CH2, which indicated that 1,10-phenan-
throline and benzene were linked by CH2.
Fig. 2 XPS spectra of the MOPs-Pd.
the binding energy (B.E.) of 337.4 eV and 342.4 eV, which are
assigned to be Pd 3d5/2 and 3d3/2 of Pd (+2), respectively.
Compared with the PdCl2 (337.9 eV and 343.1 eV), the Pd2+
binding energy in the MOPs-Pd-I catalyst shis negatively by
0.5 eV and 0.7 eV. This can be attributed to the effect of the
coordination with 1,10-phenanthroline in microporous
networks. The results show that Pd2+ can be immobilized
successfully on the MOPs by coordinating to 1,10-phenanthro-
line rather than by physical adsorption of Pd2+ on the surface.
XPS graphs of MOPs-Pd-II also reveal that Pd2+ is immobilized
on MOPs materials.
The surface area and pore structure of the MOPs and MOPs-
Pd were investigated by nitrogen adsorption analyses at 77.3 K.
In Fig. 3, the MOPs-Pd exhibits type I adsorption–desorption
isotherms, which is similar to the isotherms exhibited by the
parent MOPs polymers. The result implies that these micropo-
rous organic polymers and metalized polymers consist of both
micropores and mesopores. The apparent Brunauer–Emmett–
Teller surface areas (SBET) of MOPs-Pd are smaller than those of
the non-metallized parent networks (Table 1), which can be
attributed to both the partial pore lling with metal and simple
increase in mass. However, the materials are still signicantly
The X-ray photoelectron spectroscopy (XPS) analysis of the
MOPs-Pd is performed to investigate the coordination states of
palladium species (Fig. 2). In Fig. 2, the Pd 3d XPS spectra of the
MOPs-Pd-I catalysts reveal that Pd is present in the +2 oxidation
state rather than in the metallic state. This is corresponding to
Fig. 3 N2 adsorption–desorption isotherms and corresponding pore
Fig. 1 FT-IR spectra of MOPs and MOPs-Pd.
34596 | RSC Adv., 2019, 9, 34595–34600
size distributions of MOPs and MOPs-Pd.
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Table 1 Physical properties of MOPs and MOPs-Pd
SBETa [m2 gꢀ1
]
SMicrob [m2 gꢀ1
]
VMicro [m3 gꢀ1
]
[Pd]d [wt%]
c
Sample
MOPs-I
MOPs-Pd-I
MOPs-II
761
744
664
623
447
422
506
502
0.211
0.199
0.225
0.225
—
2.5
—
MOPs-Pd-II
2.4
a
b
Surface area calculated from the nitrogen adsorption isotherm using the BET method. The micropore volume derived using a t-plot method
c
d
based on the Halsey thickness equation. Total pore volume at P/P0 ¼ 0.99. Data were obtained by inductively coupled plasma mass
spectrometry (ICP-AES).
microporous because of many micropore surface (SMicro) and a high degree of dispersion. Meanwhile, C, N, Pd and Cl are
micropore volume (VMicro) in these materials. The abundant observed from these images, implying those are the major
micropores with a suitable size favored naturally the dispersion elements to construct the MOPs-Pd catalyst.
of the metal species. The presence of a spot of mesopore and
Then, we investigated the activities of the MOPs-Pd catalysts
macropore structure in the heterogeneous catalyst is also to determine the potential relationships between the structure
essential, because these structures enabled the frameworks to and catalyst activity. To check the catalytic activity of the MOPs-
be highly soaked in a certain solvent. As a result, the accessi- Pd in the Heck coupling reaction, iodobenzene 1a and ethyl
bility of the catalytically active sites toward the substrates is acrylate 2a were taken as the model substrate in presence of
maximized. The ICP-AES analysis indicates that the content of MOPs-Pd catalyst for optimization of the reaction condition.
Pd in MOPs-Pd I and II are 2.5 and 2.4 wt% (Table 1), First, the reaction of 1a with 2a was carried out in the present of
respectively.
Et3N with MOPs-Pd-I as catalysis in EtOH under reex to afford
The thermal stability of the MOPs and MOPs-Pd was also 3a in 75% yield. Then, a series of experiments was carried out to
assessed by TGA. The TGA traces obtained from MOPs and screen the reaction conditions, including catalysis, base,
MOPs-Pd are shown in Fig. 4. The data analysis has been per- solvent, and reaction temperature. The optimal results were
formed, and results are also shown in Fig. 4. These results show obtained when the reaction of 1a with 2a was carried out in the
that MOPs and MOPs-Pd exhibit good thermal stability in present of Et3N with MOPs-Pd-I as catalysis in DMF at 120 ꢁC for
nitrogen. It is obvious to see that the T5% and T10% of the MOPs- 1.5 h to afford 3a in 96% yield. Under the optimal conditions,
II and MOPs-Pd-II are lower compared with MOPs-I and MOPs- we carried out a series of reactions of 1 with 2 aiming to
Pd-I. This is because of the large amount CH2 in MOPs-I and determine its scope. As shown in Table 2, the MOPs-Pd-I cata-
MOPs-Pd-I.
lyzed reaction proved to be suitable for a series of 1 and 2
MOPs and MOPs-Pd were subjected to SEM and TEM anal- bearing varied groups, affording the corresponding substituted
yses, and the results are shown in Fig. 5 and 6. We can see 3a–o (entry 1–15) in very high yields.
a large number of pores in MOPs and MOPs-Pd from the SEM
To determine the active catalyst, we did two experiments in
imagines, and uniformly distributed Pd nanoparticles in MOPs- the same condition as Table 2, entry 1. Those two reactions were
Pd from the TEM images. No remarkable change in terms of the quenched aer the reaction carried out for 20 minutes. Then,
morphology of the materials occurs aer loading the palladium we separated one of the reactions, where the yield of compound
species. Then, scanning electron microscopy elemental
mapping was employed to investigate the composition of MOPs-
Pd. The results are shown in ESI† (Section IV). Obviously, the
metal Pd in MOPs-Pd-I and II are distributed in the support with
Fig. 4 TGA curves of MOPs and MOPs-Pd.
Fig. 5 SEM image of MOPs and MOPs-Pd.
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Recovery and recycling of solid heterogeneous catalysts is
one of the major concerns in metal-supported catalysis, while
supported metal catalyst usually undergo leaching of metal
species to solution.29 Thus, we investigated the recycling
performance in Heck reaction, and the results are shown in
Fig. 7. The reaction was conducted in the present of Et3N with
MOPs-Pd as catalysis in DMF at 120 ꢁC for 1.5 h. Then, the
catalyst was recovered by ltering, washing with water and ethyl
acetate. Finally, the recovered catalyst was dried in an oven for
2.0 h. Aer six runs, the reused MOPs-Pd-I and II are still
capable of catalyzing the reaction in 93% and 91% yield,
respectively. This clearly reveals a slight decrease in catalytic
activity and product yield. In addition, the morphology of
recovered catalyst was analyzed by the SEM (see ESI,† Section
IV), and the results show that there is no remarkable change in
terms of the morphology of the materials. The contents of Pd in
recovered MOPs-Pd-I and II were 2.3% and 2.1% by ICP-AES,
implying a slight leaching of palladium species.
To extend the utility of MOPs-Pd in the carbon–carbon
coupling reactions, we examined other organic reactions.
Suzuki–Miyaura reaction is an important palladium-catalyzed
cross coupling in organic synthesis. Therefore, we examined
the MOPs-Pd catalysts in Suzuki–Miyaura reaction. First, the
reaction of 1a with 4a was put together in the present of K3PO4
and MOPs-Pd-I in MeOH under reex. As monitored by TLC, the
reaction proceeded smoothly and the yield of 5a reached 91%.
Then we investigated the optimization of the reaction condi-
tions, including catalysis, base, solvent, and reaction tempera-
Fig. 6 TEM image of MOPs and MOPs-Pd.
Table 2 Heck reaction catalysed by MOPs-Pd-Ia
ture. A series of experiments revealed that EtOH/H2O (VEtOH
/
VH O ¼ 2 : 1) was effective for the synthesis of 5a. The yield of 5a
2
reached 97% when the reaction of 1a with 4a was performed in
the present of K3PO4 with MOPs-Pd-I as a catalyst at 80 ꢁC for 1.0
hour. In this reaction, the MOPs-Pd-I catalyst also can be reused
for 5 times with no signicant decrease in activity and the Pd
content of the recovered catalyst is 2.36% by ICP-AES.
Entry
R1
R2
R3
3
Yieldb (%)
1
2
3
4
5
6
7
8
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Me
Et
Et
Et
Et
Et
Et
Et
Et
Me
Me
Bu
Bu
H
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3k
3l
3m
3n
3o
96
98
97
95
93
93
94
97
98
95
97
94
94
95
90
4-Me
4-MeO
4-Cl
4-NO2
4-CN
3-Me
3,5-(Me)2
H
3-Me
H
3-Me
H
Under the optimal conditions, we carried out a series of
reactions of 1 with 4 aiming to determine its scope. In Table 3,
a range of halogenated benzene 1 and aryl boronic acid 4 with
electron-donating group and electron-withdrawing group were
applied to the conditions in parallel, affording the corre-
sponding substituted biphenyl 5b–i in high yields. It is worth
9
10
11
12
13
14
15
4-Me
4-MeO
H
Me
a
Reaction conditions: 1a (2.5 mmol), 2a (3.7 mmol), Et3N (3.7 mmol),
b
MOPs-Pd-I (50 mg, 0.28 mol%), DMF (10 mL), 120 ꢁC, 1.5 h. Isolated
yields.
3a is 61%. In another reaction, the heterogeneous catalyst was
separated from the reaction mixture by ltering, and then the
reaction liquid was allowed to react for another 70 minutes
under the same conditions. No signicant change in the yield of
compound 3a, indicating that the catalyst for the reaction was
not the dissolved Pd species leached from the heterogeneous
catalyst.
Fig. 7 Recycle test of MOPs-Pd in Heck reaction.
34598 | RSC Adv., 2019, 9, 34595–34600
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Table 3 Suzuki–Miyaura reaction catalysed by MOPs-Pd-Ia
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1
2
3
4
5
6
7
8
H
H
H
H
H
H
H
H
4-Me
4-OMe
4-CN
H
I
I
I
I
I
I
I
I
I
I
I
Br
H
5a
5b
5c
5d
5e
5f
5g
5h
5d
5i
97
96
99
98
96
95
97
95
98
99
94
92
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2-Me
3-Me
4-Me
2 F
3 F
4 F
4-CN
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5h
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when aryl bromide was used in the reaction (entry 12).
In summary, a simple and low-cost method for synthesis of
palladium complexes supported on microporous organic poly-
mers was described. The MOPs-Pd catalysts were constructed
based on highly stable microporous material, and characterized
by FT-IR, TGA, SEM, TEM, N2 sorption, XPS and ICP. These
heterogeneous catalysts displayed outstanding catalytic activi-
ties in Heck reaction and Suzuki coupling reaction. In these
reactions, the MOPs-Pd catalyst was easily recovered and reused
without loss of catalytic activity. The potential utilization and
application of these heterogeneous catalysts are currently under
investigation in our laboratory.
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Acknowledgements
This research was nancial supported by the Natural Science
Foundation of Hunan Province (no. 2018JJ3409), Scientic
Research Fund of Hunan Provincial Education Department (no.
17B207), Huaihua Science and Technology Plan Project
(2018G2201) and the construct program of the key discipline in
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