A catalytic system with high efficiency and recyclability based on Suzuki and Heck reaction in aqueous admicellar medium

Article abstract of DOI:10.1002/aoc.5495

A recyclable and non-phosphine solid palladium (II) catalyst was prepared and characterized by HR-MS, FT-IR, XPS, EDS, TGA, SEM, TEM and ICP. The Pd-catalyst exhibited high-performance catalytic activity in Suzuki and Heck C-C coupling reactions in an environmentally benign water medium. Further, the Pd-catalyst (Z₄) can be reused for 15 times with little decrease of activity through simple and efficient recovery. In addition, the turn-over number (TON) of Pd- catalyst can reach 380 at room temperature. These results proved that the Pd-catalyst has a stable structure and can be recycled many times, making the process sustainable.

Full text of DOI:10.1002/aoc.5495

Received: 7 August 2019
DOI: 10.1002/aoc.5495
Revised: 18 December 2019
Accepted: 25 December 2019
F U L L P A P E R
A catalytic system with high efficiency and recyclability
based on Suzuki and Heck reaction in aqueous admicellar
medium
Hao Zhang1,2 | Ji-Hua Zhu1,2 | Fei Hou1,2 | Zheng-Jun Quan1,2
Xi-Cun Wang1,2
|
1College of Chemistry and Chemical
A recyclable and non-phosphine solid palladium (II) catalyst was prepared and
characterized by HR-MS, FT-IR, XPS, EDS, TGA, SEM, TEM and ICP. The
Pd-catalyst exhibited high-performance catalytic activity in Suzuki and Heck
C-C coupling reactions in an environmentally benign water medium. Further,
the Pd-catalyst (Z4) can be reused for 15 times with little decrease of activity
through simple and efficient recovery. In addition, the turn-over number
(TON) of Pd- catalyst can reach 380 at room temperature. These results proved
that the Pd-catalyst has a stable structure and can be recycled many times,
making the process sustainable.
Engineering, Northwest Normal
University, Lanzhou, Gansu, 730070,
People's Republic of China
2Gansu International Scientific and
Technological Cooperation Base of Water-
Retention Chemical Functional Materials,
Lanzhou, Gansu, 730070, People's
Republic of China
Correspondence
Xi-Cun Wang, College of Chemistry and
Chemical Engineering, Northwest Normal
University, Lanzhou, Gansu 730070,
People's Republic of China.
K E Y W O R D S
aqueous admicellar medium, heck reaction, Pd-catalyst, Suzuki reaction
Email: wangxicun@nwnu.edu.cn
Zheng-Jun Quan, Gansu International
Scientific and Technological Cooperation
Base of Water-Retention Chemical
Functional Materials, Lanzhou, Gansu
730070, People's Republic of China.
Email: quanzhengjun@hotmail.com
Funding information
Key Talent Projects of Gansu Province,
Grant/Award Number: [2019]39; National
Nature Science Foundation of China,
Grant/Award Number: 21562036
1 | INTRODUCTION
catalytic performance, they suffer from high cost, toxic,
unrecoverable and unstable phosphane ligands.
Pd-catalyzed C-C cross-coupling reactions have been
emerged as a versatile tool in organic synthesis.[1–3] Such
as Suzuki-Miyaura and Mizoroki-Heck cross-coupling
reactions have been become essential methods in the syn-
thesis of biaryl and aryl olefinic compounds.[4] In general,
these reactions were usually carried out in the presence
of Pd-phosphine complexes.[5–7] Despite their excellent
Nowadays, the environmental awareness encourages
more friendly chemical processes. Researchers have
begun to implement green chemistry practices using of
new recyclable, heterogeneous or phosphine-free cata-
lysts. In detail, they have developed palladium catalysts
using nitrogen containing,[8,9] N-heterocyclic carbenes,
oximes,[10] and imines ligands,[11] and so on.
Appl Organometal Chem. 2020;e5495.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5495

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ZHANGA ET AL.
Now, there is a necessary to design new catalysts that
3 | RESULT AND DISCUSSION
can retain the selectivity and activity of homogeneous
catalysts and also can be removed from the reaction mix-
ture, and reused following appropriate washing pro-
cesses.[12] The usually used method was to immobilize
palladium complexes on various supports.[13–17] So far,
polymer-supported palladium catalyst and self-assembled
imidazole-palladium catalysts have been developed for
the Suzuki and Heck coupling reactions in water with
high efficiency and recyclability.[18,19] Recently, we have
developed a salen-type palladium (II) catalyst (Z4) that
exhibits excellent catalytic activity for Suzuki and Heck
cross-coupling reactions under mild conditions
(Figure 1). The steric environment adjacent to the nitro-
gen atom in the ligand parts enhanced the thermal stabil-
ity of the palladium species.[20] On the other hand,
increasing the donor capacity and steric bulk of the
ligand should favor the oxidation addition and reduction
elimination steps in the catalytic cycle, respectively.[21]
Moreover, these two factors also promote the activation
of the catalyst, which involves the formal reduction of the
Pd (II) precatalyst to the Pd(0) active species.[22] Thus,
these made the Pd-catalyst have an excellent catalytic
activity with recyclability.
3.1 | Preparation and characterization of
the catalyst
Firstly, the Pd-catalyst (Z4) was prepared by a four-step
procedure[25] (see SI Scheme S1). The Pd-catalyst has a
ꢀ
high melting point above 290 C, and its poor solubility
in organic solvents was observed, which enable the cata-
lyst to be a solid catalyst for organic reactions. The struc-
ture of the pd-catalyst is characterized using different
techniques such as HR-MS, FT-IR, XPS, EDS, TGA,
FE-SEM, TEM and ICP. In the 1H NMR spectrum of
ligand (Z3), a peak representing the hydroxyl proton reso-
nated at δ 13.61 ppm, and some peaks corresponding to
other protons are also shown. Unfortunately, NMR spec-
tra were not recorded due to poor solubility of pd-catalyst
(Z4) in all accessible solvents (include CDCl3, DMSO-d,
DMF-d, THF-d8, (CD3)2CO, CD3CN, D2O). A peak at m/z
1111.2957 in the HR-MS spectrum of Pd-catalyst (Z4)
corresponding to the [M + H]+ ion further confirmed the
structure of Pd-catalyst (Z4). (See SI Figure S1).
Meanwhile, the replacing dangerous, and expensive
organic solvents with water are an important subject
from a different perspective. In recent years, water
has been applied to an array of organic reactions
because it is a safe, abundant and a green reaction
medium.[23] To realize the high catalytic performance
in water, a method by adding phase-transfer agents
have been reported.[24] Herein, we prepared a pd-
catalyst (Z4) (Figure 1) as a recyclable, heterogeneous
and phosphine-free catalyst for Suzuki and Heck reac-
tions under environmentally friendly conditions. More-
over, the reaction can be completed in aqueous
admicellar medium in the presence of SDS (Sodium
dodecyl sulfate)/K2CO3.
3.2 | FT-IR spectroscopy and X-ray
photoelectron spectroscopy (XPS) analysis
The FT-IR was employed to give a detailed investigation
of the ligand (Z3) and the pd-catalyst (Z4). The
Figure 2(A) exhibited a broadband at 3439 cm−1 corre-
spond to the -OH group with the ligand (Z3), and it was
indicated from strong IR band appeared at 1620 cm−1
due to the C=N vibrations. In the FT-IR spectrum of
Figure 2(B), the C=N peak was shifted to 1608 cm−1, and
the peak in the region of 3439 cm−1 (-OH stretch) dis-
appeared.[26] These suggested that complete complexa-
tion with the palladium had occurred through
the nitrogen of the C=N group and oxygen of the -OH
group.
The XPS elemental survey scan of the surface of
ligand (Z3) and pd-catalyst (Z4) were presented in
Figure 2. As can be seen in Figure 2(C), three intense
peaks at 300, 420 and 540 eV were corresponding to C1s,
N1 s and O1s,[27] showing the existence of these three ele-
ments in ligand (Z3). Besides, the peak with binding
2 | EXPERIMENTAL
Experimental procedures, NMR spectra and other
data for this study are available in Supporting
Information.
FIGURE 1 The Pd-catalyst (Z4)
structure

A CATALYTIC SYSTEM WITH HIGH EFFICIENCY AND RECYCLABILITY
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FIGURE 2 The comparison of FT-
IR between the ligand (Z3) (A) and its
pd-catalyst (Z4) (B); XPS between the
ligand (Z3) (C) and pd-catalyst (Z4) (D),
full range; XPS signals of the Pd3d core
levels in the Pd-catalyst (Z4) (E)
energy of 350 eV was related to Pd3d, as shown in
Figure 2(D). Full XPS spectra of ligand (Z3) and
pd-catalyst (Z4) contain signature peaks of different ele-
ments (Figure 2 C, 2 D). Additionally, to investigate the
oxidation state of Pd in pd-catalyst, XPS analysis was con-
ducted (Figure 2 E). The high-resolution Pd3d XPS scan
of pd-catalyst revealed the doublet peaks at the binding
energy of 337.9 eV and 343.2 eV, which can be indexed to
electron transitions of 3d5/2 and 3d3/2 of Pd, respec-
tively. This result confirmed that the chemical state of
palladium is +2 in pd-catalyst and palladium (II) was not
reduced during the preparation of the Pd-catalyst. The
binding energy peak affirms the formation of Pd
(II)-complex.
0.381 mmol/g−1 as determined using ICP-OES analysis
(23% leaching).
3.4 | Thermogravimetric analysis
Thermogravimetric analysis (TGA) was performed to
study the thermal stability of the ligand(Z3) and
ꢀ
Pd-catalyst(Z4), using a heating rate of 10 C/min under
a nitrogen atmosphere between 30 ꢀC and 600 ꢀC (See SI
Figure S3). The loss of hydroxyl groups resulted in a
weight loss of 5% between 126.3 ꢀC for ligand (Z3)
(Figure S3A), whereas loss of covalently bonded organic
moieties at a temperature up to 312 ꢀC resulted in a
weight loss of 29%, whereas the pd-catalyst (Z4) showed
decomposition in two stages (Figure S3B). The loss of 4%
ꢀ
3.3 | Energy-dispersive spectroscopy
at a temperature up to 188.9 C forms the first stage; loss
(EDS) analysis
of covalently bonded organic moieties at a temperature
up to 350.6 ꢀC resulted in a weight loss of 15%. Obviously,
the pd-catalyst (Z4) was stable at higher temperatures,
which is also possible to be used as a catalyst in higher-
temperature organic reactions.
Furthermore, the ligand (Z3) and pd-catalyst (Z4) were
examined using EDS analysis to determine the chemical
composition (SI Figure S2). The EDS mapping images in
Figure S2(B) revealed the presence of O, N, C and
importantly Pd elements in the pd-catalyst (Z4) structure,
the amount of palladium obtained from EDS analysis is
around 13.76 (wt %). However, EDS pattern in
Figure S2(A) indicated the presence of O, N and C ele-
ments in ligand (Z3). Meanwhile, the amount of loaded
Pd was determined to be 0.498 mmol/g−1 using induc-
tively coupled plasma optical emission spectrometry
(ICP-OES). Another catalytic experiment was further
conducted to estimate the impact of Pd leaching. The
amount of Pd remaining after the 15 cycles was
3.5 | Field emission-scanning electron
microscopic (FE-SEM) and transmission
electron microscopy (TEM) analysis
To gain more insight into the Pd-complex catalyst, and
survey the size, shape and surface morphology of ligand
(Z3) and pd-catalyst (Z4), the FE-SEM and TEM
(Figure 3) technology were used. The SEM images in
Figure 3(A) showed that the ligand (Z3) displayed a

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ZHANGA ET AL.
FIGURE 3 The SEM micrographs
of ligand (Z3) (A), pd-catalyst (Z4) (B);
TEM micrographs of ligand (Z3) (C), Pd-
catalyst (Z4) (D)
uniform and nearly a fusiform shape. At the same time,
Figure 3(B) displayed that fresh Pd- catalyst (Z4) has a
monodispersed with diameter of about 0.32–0.63 μm. The
observed SEM images demonstrated the morphological
and characteristic distinct vision between the ligand and
the Pd-catalyst due to the change in the coordination of
ligand (Z3) with palladium by the coordination bond. The
morphologies of the ligand (Z3) and pd-catalyst (Z4) were
found out by transmission electron microscopy (TEM).
TEM image Figure 3(C) indicated a uniform and nearly a
fusiform shape of ligand (Z3) was clearly observed in the
TEM image. After ligand (Z3) was coordinated with palla-
dium through a coordination bond, and then in Figure 3
(D), obvious Pd species on the surface of pd-catalyst (Z4)
was observed[26]. Furthermore, the presence of Pd ele-
ments was confirmed by EDS mapping images.
obtained in 85% yield (Table S1, entries 7). We focused
on replacing organic solvents with water. It seemed that
the presence of water increases the solubility of the base
and activates the boronic acid, thereby increasing the rate
of reaction in aqueous medium.[28] To our delight, the
reaction proceeded smoothly by adding PEG-400 and
DMF to H2O (Table S1, entries 10–15). This result was
in accordance with our previous work.[23] Even if the
amount of PEG-400 and DMF decreased from 1/1 to 1/10
the reaction was still proceeded smoothly. In water with-
out other additive the reaction to give the desired prod-
ucts in 40% yields (Table S1, entry 16). It was worth
noting that in the presence of SDS the yield of coupled
product (1) was remarkably improved. (Table S1, entries
17–22). The SDS can play an important role as the phase
transfer catalyst (PTC). The critical micelle concentration
(CMC) of SDS as an efficient surfactant was around
8000–10000 μmol L−1[29]. Next, we chose the CMC of the
SDS. Notably, when the reaction was performed in the
absence of pd-catalyst (Z4), no formation of product
coupled product (1) was observed (Table S1, entry 9).
Meanwhile, Pd (OAc)2, PdCl2(PPh3)2 and pd-catalyst
(Z6)[30] (see SI Scheme S2) as comparative catalysts gave
a very poor yield forming product coupled product (1)
under optimal conditions (Table S1, entries 23, 24, 25),
and the structure of pd-catalyst (Z6) was confirmed
according to HR-MS and FT-IR Spectroscopy analysis
(See SI Figure S4, Figure S5). This might be due to the
steric environment adjacent to the nitrogen atom of the
ligand (Z3) enhanced the thermal stability of the palla-
dium species. On the other hand, increasing the donor
capacity and steric bulk of the ligand should facilitate the
activation of the catalyst, which involved the formal
3.6 | The Suzuki–Miyaura cross-coupling
reaction
On the successful preparation of the pd-catalyst (Z4),
it's catalytical-reactivity was tested in the Suzuki
reaction. In the beginning, 4-Bromoanisole (a1) and
4-Methylbenzeneboronic (b1) were chosen as the model
substrates for the reaction (see SI Table S1). From the
initial screening, we found that the coupled product (1)
was obtained in 85% isolated yield when K2CO3 was used
as bases (Table S1, entries 1–6). Furthermore, the catalyst
loading screening showed that increasing the catalyst
loading could improve the reaction yield (Table S1,
entries 6–9). It seemed that when the Pd-catalyst (Z4)
loading was 0.25 mol%, the corresponding product was

A CATALYTIC SYSTEM WITH HIGH EFFICIENCY AND RECYCLABILITY
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reduction of the Pd (II) precatalyst to the Pd(0) active spe-
cies. Thus, these results made that the Pd-catalyst (Z4)
has an excellent catalytic activity with recyclability.
Finally, the yield was improved with the increasing of
reaction time (Table S1, entries 17–21). It was also found
that temperature has little effect on the yield of the prod-
uct (Table S1, entries 17 and 22). Therefore, the best
condition in this reaction was the combination of
pd-catalyst (Z4) as a catalyst and water as the solvent
under room temperature in the presence of SDS/K2CO3.
The scope and generality of the optimized protocol
was explored for Suzuki-Miyaura reaction by using a
variety of aryl halide and phenylboronic acids in Table 1.
The electronic nature of the coupling partner has
little influence on the reaction efficiency. Notably,
2-naphthylboronic acid also reacted efficiently with aryl
bromides to give the desired products (23–25) in good
yields. Remarkably, ortho-substituted aryl halides were
coupled with aryl boronic acids to give corresponding
products in moderate yields (76%–80%) (4, 11, 17, 18).
However, highly sterically hindered di-ortho substituted
biphenyls cannot be synthesized under the same condi-
tions (7), indicating that the catalyst was the low toler-
ance toward steric hindrance at the substrates. An
increased of reaction time and catalyst loading did not
significantly affect this behaviour. Finally, aryl chlorides
were evaluated under room temperature, but none of
them showed enough activity to give product. However,
and no change was observed. Meanwhile, the amount of
Pd remaining after the 15 cycles was 0.381 mmol g−1 as
determined using ICP-OES analysis (23% leaching).
These results proved that the Pd-catalyst (Z4) has a stable
structure and can be recycled many times with good sus-
tainability. Further, we also studied the critical reaction
parameters of catalyst (turnover numbers = TON; turn-
over frequency = TOF). Table 1 and Table 2 showed the
results of these investigations. It was possible to achieve a
TON of 380 for the reaction at room temperature (1).
These results represented a significant improvement
compared with refluxed conditions in the literature,[32]
although vale of TON is equivalent. The results showed
that the pd-catalyst (Z4) has an excellent catalytic activity
and high catalytic efficiency in the Suzuki reaction.
3.7 | The Mizoroki-heck cross-coupling
reaction
Initially, 4-Iodoanisole (c1) and Methyl acrylate (d1) were
chosen as the model substrates for Heck reaction. To our
delight, it can be observed that the yield was significant
ꢀ
enhanced to 86% at 80 C. Meanwhile, as the reaction
time was increased the yields are also improved to 88%
(See SI Table S2).
The scope and generality of the optimized protocol
was explored for Heck reaction of various aryl iodide
and bromides with olefins in Table 2. It can be
observed that aryl iodine with electron withdrawing
substituents such as -NO2, -CN, and -Cl led to high
yields of the corresponding products (29–31). Aryl
iodines with electron-donating groups like -OMe under-
went the reaction smoothly to give moderate yields of
products (28, 33, 39, 41, 44, 47). Notably, the yields of
products appeared to be influenced by the electronic
nature of the aryl group, with electron-neutral or
electron-donating aryl iodides giving lower yields than
electron withdrawing aryl iodides (28–31, 33, 39, 41, 44,
47). Interestingly, the sterically hindered naphthyl aryl
iodine, 4-tert-butyliodobenzene and 4-iodobiphenyl
afforded the desired products in good yields
(32, 37, 38). We further investigated the reaction of
2-bromothiophene with methyl acrylate, affording 89%
yield of the desired product (36) in 36 hr. Excitingly,
the reaction of aryl bromides with olefins generate
products in over 62% yield (49, 50), highlighting the
applicability of the reaction protocol in aryl bromide.
We further investigated the substrate scope of various
aryl chlorides with olefins. Unfortunately, the reaction
does not work, which indicated that the activation of
aryl chlorides was less than that of aryl iodides and
bromides.[29]
ꢀ
the reaction showed smooth reactivity at 80 C and gave
coupling product (26) and coupling product (27) in 50%
and 51% isolated yields, respectively. Indicated that aryl
chlorides were less active than aryl bromides, and their
reluctance to perform the oxidative addition to palladium
makes the coupling procedure very difficult.[31]
The recyclability of a catalyst is an important factor of
catalysis reactions. We explored the reusability of
pd-catalyst (Z4) by a simple filtration from the reaction
mixture. The catalyst showed excellent activity for 15 runs
with no appreciable change in the product yield (95–80%)
(See SI Figure S6). EDS determined the palladium ele-
ment of the Pd-catalyst (Z4) after 15 consecutive runs,
TABLE 1 Scope of the Suzuki reaction of aryl halogen with
arylboronic acids[a]
[a] Reaction conditions: r. t.; the Pd-catalyst (Z4) 0.25 mol%; 0.3 mmol of aryl
halide, 0.33 mmol of aryl boric acid, 0.6 mmol of K2CO3; 4 ml H2O, 9.2 mg
SDS; in air; 3 hr; Isolated yields; TON = (moles of product) / (moles of Pd in
the catalyst), TOF = TON/reaction time, [b] 80 ꢀC.

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ZHANGA ET AL.
TABLE 2 Scope of Mizoroki-Heck cross-coupling reaction of aryl halogen with olefins[a]
[a] Reaction conditions: the Pd-catalyst (Z4) 1.5 mol%; 0.4 mmol of aryl halide, 0.6 mmol of olefins, 0.8 mmol of K2CO3; 4 ml H2O, 9.2 mg SDS; in air; 80 ꢀC;
36 hr; Isolated yields.
[2] T. Ichitsuka, N. Suzuki, M. Sairenji, N. Koumura,
4 | CONCLUSIONS
ChemCatChem 2019, 11, 2427.
[3] M. Carril, R. SanMartin, E. Dominguez, Chem. Soc. Rev. 2008,
In summary,
a
novel non-phosphine palladium
37, 639.
(II) catalyst was successfully prepared. This Pd-catalyst
represented an excellent catalytic activity with recyclabil-
ity in catalyzing Suzuki and Heck coupling reactions in
aqueous admicellar medium. In the current system, the
catalyst loading can be as low as 0.25 mol%, and the TON
value can be 380. Meanwhile, the water solvent endows
the reaction with green and safe properties.
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ACKNOWLEDGMENTS
We are thankful for the financial support from the
National Nature Science Foundation of China
(No. 21562036) and Key Talent Projects in Gansu
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CONFLICT OF INTEREST
There are no conflicts to declare.
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SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
article.
How to cite this article: Zhang H, Zhu J-H,
Hou F, Quan Z-J, Wang X-C. A catalytic system
with high efficiency and recyclability based on
Suzuki and Heck reaction in aqueous admicellar
medium. Appl Organometal Chem. 2020;e5495.
https://doi.org/10.1002/aoc.5495
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