Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles

Article abstract of DOI:10.1016/j.inoche.2020.108368

Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.

Full text of DOI:10.1016/j.inoche.2020.108368

Inorganic Chemistry Communications 123 (2021) 108368
Contents lists available at ScienceDirect
Inorganic Chemistry Communications
journal homepage: www.elsevier.com/locate/inoche
Short communication
Synthesis of biaryl compounds via Suzuki homocoupling reactions
catalyzed by metal organic frameworks encapsulated with
palladium nanoparticles
Hong Tanga, Ming Yanga, Xin Lia, Mei-Li Zhoua, Yan-Sai Baoa, Xin-Yu Cuia, Kun Zhaob,
,
Yu-Yang Zhanga *, Zheng-Bo Hana
a College of Chemistry, Liaoning University, Shenyang 110036, PR China
b College of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016, PR China
A R T I C L E I N F O
A B S T R A C T
Keywords:
Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocou-
pling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted
with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to
produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of
metal organic frameworks encapsulated with palladium nanoparticles (Pd@MOFs). This strategy for forming
symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation,
good recyclability and no addition of toxic halogenated benzene.
Heterogeneous catalysis
Homocoupling reaction
Metal organic frameworks
Palladium nanoparticles
Suzuki reaction
1. Introduction
Therefore, as long as there are two catalytic sites of Pd(0) and Cu(II),
phenylboronic acids could synthesize biaryl compounds via
Iodination-Suzuki tandem reaction.
a
Homocoupling reaction of phenylboronic acids is an important
strategy for forming symmetric C-C bond between benzene rings [1–3].
Symmetrical biaryls are of great significance in versatile applications of
drugs, dyes, agrochemicals, semi-conductor and optically active ligands
[4–7]. Homocoupling reaction of phenylboronic acids catalyzed by
different catalysts has been extensively reported such as Pd(OAc)2 [8],
Cu(BDC) [9], the clay encapsulated Cu(OH)x [10], gold nanoparticles
[2,11], Fe3O4 nanoparticle-supported Cu(II)-β-cyclodextrin complex
[12], and so on. They can be divided into two types. One is a homoge-
neous catalyst such as Pd(OAc)2 reported by Dwivedi et al. [8], which is
difficult to separate and recycle and easy to cause metal pollution. The
other is a heterogeneous catalyst such as Cu(BDC) reported by Puthiaraj
et al. [9], which is not very stable and efficient.
Metal organic frameworks (MOFs) composed of metal ions and
organic linkers have received extensive attention in recent years
[23–26]. Owing to their ordered porous structures, large specific surface
areas and certain chemical and thermal stability, MOFs were widely
used in heterogeneous catalysis, gas storage and separation, drug de-
livery and so on [27–32]. Especially, there are several typical MOFs with
excellent performance and wide application, such as MIL-101(Cr) [33],
UiO-66(Zr) [34], HKUST-1(Cu) [35], ZIF-8(Zn) [36]. All of them are
common carriers for Pd nanoparticles. Pd@HKUST-1 is a ideal bifunc-
tional heterogeneous catalyst that both palladium nanoparticles and
copper ions are evenly and stably distributed on it [31,37]. Porous
structure materials often have better catalytic performance, because the
catalysts with porous structure have larger contact areas with the re-
actants, more exposed catalytic sites, and certain adsorption, as the same
conclusion of Chen and Hou et al. [38,39].
Heterogeneous Suzuki cross-coupling catalysts has been extensively
reported [13–18], due to their highly efficiency and stability. A typical
Suzuki reaction is phenylboronic acid coupled with halogenated ben-
zene, catalyzed by zero-valent palladium complex [19]. Among all of the
halogenated benzenes, iodobenzene is the most suitable for Suzuki re-
action [20]. More importantly, iodobenzenes can be synthesized from
phenylboronic acids catalyzed by various forms of Cu(II) [21,22].
Tandem reactions catalyzed by metal organic frameworks have been
reported widely [40–43]. Based on this, we have designed a new
homocoupling route of phenylboronic acid, using Pd@HKUST-1 as a
bifunctional heterogeneous catalyst. This route is divided into two steps.
* Corresponding author.
E-mail address: yyzhang@lnu.edu.cn (Y.-Y. Zhang).
https://doi.org/10.1016/j.inoche.2020.108368
Received 13 October 2020; Received in revised form 22 November 2020; Accepted 23 November 2020
Available online 1 December 2020
1387-7003/© 2020 Elsevier B.V. All rights reserved.

H. Tang et al.
Inorganic Chemistry Communications 123 (2021) 108368
Scheme 1. Reaction route.
adding toxic halogenated benzene (see Scheme 1).
HKUST-1 was synthesized by the hydrothermal method.
Pd@HKUST-1 was prepared via a simple capillary impregnation-
reduction method. The catalyst has been characterized by X-ray
diffraction (XRD), scanning electron microscope (SEM), transmission
electron microscopy (TEM), energy-dispersive spectra (EDS), thermog-
ravimetric analysis (TGA). The specific surface areas and pore volumes
of the catalyst were determined by N2 physisorption measurements.
Inductively coupled plasma atomic emission spectroscopy (ICP-AES)
was used to determine the content of Pd in Pd@HKUST-1. The conver-
sions and yields of the catalytic reactions were analyzed by GC. Proton
NMR spectra (1H NMR, 300 MHz, CDCl3) was used to further verify the
structure of the tandem reaction product.
2. Experimental
The experimental section is described in detail in Supplementary
information.
3. Results and discussion
Fig. 1. PXRD patterns of simulated (black), HKUST-1 (magenta), Pd@ HKUST-
1 (red). (For interpretation of the references to colour in this figure legend, the
reader is referred to the web version of this article.)
3.1. Characterization of catalysts
The powder XRD patterns of HKUST-1 and Pd@HKUST-1 are dis-
played in Fig. 1. The PXRD pattern of as-synthesized HKUST-1 matched
well with the already reported PXRD patterns [44], which suggested that
HKUST-1 was obtained. After loading of Palladium nanoparticles, there
was no apparent loss of crystallinity in PXRD patterns (Fig. 1), which
demonstrated that the frameworks of HKUST-1 are mostly maintained,
similar to the results reported previously [45]. Scanning electron mi-
croscope (SEM) was performed to observe the morphologies of
Pd@HKUST-1 before and after catalysis. As shown in Fig. 2 (a) and (b),
The first step is Cu(II) to catalyze one part of phenylboronic acid with I2
to synthesize iodobenzene. The second step is Pd(0) to catalyze the
another part of phenylboronic acid coupled with iodobenzene to syn-
thesize biphenyl. Both of them are catalyzed by the same heterogeneous
catalyst. Compared to the conventional homogeneous catalysis homo-
coupling reaction of phenylboronic acids, this strategy for forming
symmetric C-C bond between benzene rings has obvious advantages of
separating catalysts. Compared to the Suzuki reaction to form symmetric
C-C bond between benzene rings, this strategy has advantages of no
Fig. 2. (a) SEM image of as-synthesized Pd@HKUST-1 before catalysis reaction; (b) SEM image of Pd@HKUST-1 after catalysis reaction.
2

H. Tang et al.
Inorganic Chemistry Communications 123 (2021) 108368
Fig. 4. (a) N2 adsorption isotherms at 77 K of as-synthesized HKUST-1 and
Pd@HKUST-1. (b) Pore size distribution of as-synthesized HKUST-1 and
Pd@HKUST-1.
crystals of regular octahedron could be observed before and after
catalysis, indicating that the structure of Pd@HKUST-1 was stable.
Transmission electron microscopy (TEM) was performed to observe the
loading of palladium nanoparticles. Fig. 3 (a) demonstrated that palla-
dium nanoparticles were successfully uniformly loaded on HKUST-1.
Fig. 3 (c) showed that palladium nanoparticles were stable after catal-
ysis. Fig. 3 (b) and (d) showed that the size of palladium nanoparticles
was mainly at ~1.8 nm before and after catalysis. As shown in Fig. S1
the EDS further confirmed the presence of Cu and Pd in the catalyst. The
loading amount of Pd was 0.97 wt% determined by ICP-AES. N2
adsorption isotherms and pore size distribution of as-synthesized
HKUST-1 and Pd@HKUST-1 are showed in Fig. 4. The N2 sorption
properties of samples was analyzed by the Brunauer-Emmett-Teller
(BET) method at 77 K. It showed that HKUST-1 has a large BET spe-
cific surface area of 971 m2/g. After the Pd on the load, the BET specific
surface area is significantly reduced to 461 m2/g. The total pores vol-
umes of HKUST-1 and Pd@HKUST-1 are 0.54 mL/g and 0.41 mL/g,
respectively. The average pores diameters (4 V/A by BET) of HKUST-1
and Pd@HKUST-1 are 2.2 nm and 3.6 nm, respectively. In addition, as
shown in Fig. S2, TG analysis showed that the catalysts were of high
thermal stability below 350 ◦C. After the catalyst was cycled five times,
the reaction supernatant was taken and no leakage of Pd was detected by
ICP-AES.
Fig. 3. (a) TEM image of as-synthesized Pd@HKUST-1 before catalysis reac-
tion; (b) corresponding size distribution of Pd nanoparticles before catalysis
reaction; (c) EM image of Pd@HKUST-1 after catalysis reaction; (d) corre-
sponding size distribution of Pd nanoparticles after catalysis reaction.
3

H. Tang et al.
Inorganic Chemistry Communications 123 (2021) 108368
Fig. 5. Product analysis of phenylboronic acid reaction. (The solvent was
Scheme 2. Mechanism of Cu catalyzed iodination reaction of phenyl-
acetonitrile and the temperature was 343 K.)
boronic acid.
Table 1
Reaction of different conditions.
Entry catalyst
Base
T(◦C) solvent
Yield3a (%) Yield4a (%)
0
1
Cu(NO3)2⋅3H2O
HKUST-1
/
/
60
60
acetonitrile 84.2
2
acetonitrile 7.1
0
3
Cu(NO3)2⋅3H2O K2CO3 60
acetonitrile 99.9
acetonitrile 42.5
acetonitrile 25.1
acetonitrile 16.7
acetonitrile 59.3
acetonitrile 78.4
0
4
HKUST-1
K2CO3 60
K2CO3 60
0
5
None
0
6
Pd@HKUST-1
Pd@HKUST-1
Pd@HKUST-1
Pd@HKUST-1
Pd@HKUST-1
Pd@HKUST-1
Pd@HKUST-1
Pd@HKUST-1
/
60
0
7
K2CO3 60
K2CO3 70
K2CO3 70
K2CO3 70
K2CO3 70
K2CO3 70
K2CO3 70
26.3
20.6
80.5
25.4
42.6
81.8
5.4
8
9
Ethanol
DMF
18.5
55.1
56.5
17.2
0
10
11
12
13n
DMSO
Toluene
Ethanol
Reaction conditions: 1a (2 mmol phenylboronic acid), 2 (0.5 mmol I2), n (no I2),
catalyst, K2CO3 (0.7 mmol), solvent (5 mL), N2 (1 bar), 7 h, Yields was deter-
mined by GC with internal standard (1 mmol n-dodecane).
Scheme 3. Mechanism of Pd catalyzed Suzuki coupling reaction.
3.2. Catalytic tests
Table 1), but the conversion of phenylboronic acid had not reached
◦
◦
100%. So increasing the temperature from 60 C to 70 C, and it was
monitored that the conversion of phenylboronic acid reached almost
100%. (Entry. 8, Table 1) Different solvents were tested, and ethanol and
toluene were more conducive to the formation of biphenyl among the
solvents investigated (Entry. 8–12, Table 1). Besides, in the absence of
iodine, homocoupling reaction of phenylboronic acid catalyzed by
Pd@HKUST-1 had a very low yield (Entry. 13, Table 1). The mechanism
of the Suzuki reaction see Scheme 3.
A series of catalytic tests were carried out to explore the best con-
ditions for this tandem reaction. As shown in Fig. 5, in a typical phe-
nylboronic acid reaction it was detected that the yield of iodobenzene
increased at first and then decreased, meanwhile the yield of biphenyl
gradually increased. The step of phenylboronic acid to iodobenzene was
the focus of discussion. Firstly, consistent with previous reports [24,28],
copper ions had good catalytic activity (Entry. 1, Table 1) as a homo-
geneous catalyst. The mechanism of the iodination reaction of phenyl-
boronic acid catalyzed by Cu(II) is illustrated in Scheme 2 [46]. HKUST-
1 as a Cu-MOF had poor catalytic effect (Entry. 2, Table 1), maybe
because of steric hindrance. However, when the Suzuki reaction cocat-
alyst inorganic base was added, the catalytic effects of copper ions and
HKUST-1 were both improved (Entry. 3 and 4, Table 1). Under indi-
vidual effect of the inorganic base, somewaht iodobenzene was formed
(Entry. 5, Table 1). Pd@HKUST-1 had better catalytic efficiency than
HKUST-1 (Entry. 6 and 2, Table 1). When all factors including Pd, Cu-
MOFs and inorganic bases were combined, the catalyst could achieve
the conversion of a large amount of phenylboronic acid (Entry. 7,
Under the same conditions, yields of iodobenzenes and biphenyls
with different groups at 7 h were displayed. Ethanol was selected as an
efficient and environmentally friendly organic solvent for the tandem
reaction. Almost all phenylboronic acids with different groups smoothly
reacted to provide the desired products. For unsubstituted phenyl-
boronic acid, the yield of biphenyl was 81% (Entry. 1, Table 2). Firstly,
the case of electron-withdrawing group was discussed. The yield of 2,2-
difluorodiphenyl acid was 69% (Entry. 2, Table 2). When the group of
meta- phenylboronic acids was a -F or -Cl, the yields of products were
raised to 91.4% and 92.8% (Entry. 3 and 5, Table 2). When the group of
4

H. Tang et al.
Inorganic Chemistry Communications 123 (2021) 108368
Table 2
Tandem reaction of different reactants.
Entry
1
Reactant
Product
Yield3 (%)
18.0
Yield4 (%)
81.0
2
3
30.1
7.6
68.9
91.4
4
5
9.7
6.2
89.3
92.8
6
7.7
91.3
7
8
17.4
40.6
15.3
58.4
9
22.7
71.0
76.3
28.0
10
11
50.8
48.2
Reaction conditions: 1 (2 mmol phenylboronic acid), 2 (0.5 mmol elemental iodine), catalyst (1 mmol % Pd), base (0.7 mmol), solvent (5 mL ethanol), N2 (1 bar), 70 ◦C,
7 h, Yields was determined by GC with internal standard (1 mmol n-dodecane).
5

H. Tang et al.
Inorganic Chemistry Communications 123 (2021) 108368
the work reported in this paper.
Acknowledgment
This work was granted financial support from the National Natural
Science Foundation of China (Grant 21671090), Research Fund of
Liaoning Provincial Department of Education (2017LQN18). The au-
thors gratefully thank the Collaborative Innovation Group of Clean En-
ergy Resources for kind help in catalyst characterization.
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://doi.
org/10.1016/j.inoche.2020.108368.
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