The synthesis of SBA-Pr-3AP@Pd and its application as a highly dynamic, eco-friendly heterogeneous catalyst for Suzuki–Miyaura cross-coupling reaction

Article abstract of DOI:10.1007/s11164-020-04218-4

The hexagonal mesoporous organic–inorganic hybrid as a new nanocatalyst was prepared by the treatment of SBA-15 with (3-chloropropyl)triethoxysilane, the 2,4,6-triamino pyrimidine ligand, and then PdCl₂ to obtain the SBA-15-propyl-triamino pyrimidine@Pd called as SBA-Pr-3AP@Pd, which was examined through Suzuki–Miyaura cross-coupling reaction by several aryl halides and phenylboronic acid under mild conditions in high yield.

Full text of DOI:10.1007/s11164-020-04218-4

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-020-04218-4
The synthesis of SBA‑Pr‑3AP@Pd and its application
as a highly dynamic, eco‑friendly heterogeneous catalyst
for Suzuki–Miyaura cross‑coupling reaction
Fatemeh Mohajer1 · Ghodsi Mohammadi Ziarani1 · Alireza Badiei2
Received: 22 April 2020 / Accepted: 20 July 2020
© Springer Nature B.V. 2020
Abstract
The hexagonal mesoporous organic–inorganic hybrid as a new nanocatalyst was
prepared by the treatment of SBA-15 with (3-chloropropyl)triethoxysilane, the
2,4,6-triamino pyrimidine ligand, and then PdCl2 to obtain the SBA-15-propyl-tri-
amino pyrimidine@Pd called as SBA-Pr-3AP@Pd, which was examined through
Suzuki–Miyaura cross-coupling reaction by several aryl halides and phenylboronic
acid under mild conditions in high yield.
Keywords Decorated mesoporous silica · Suzuki–Miyaura cross-coupling ·
Heterogeneous nanoporous catalyst · 2,4,6-Triamino pyrimidine ligand · SBA-Pr-
3AP@Pd
Introduction
The application of the nanoreactor as the particular nanochemical compounds
such as dendrimers [1], carbon nanotubes [2], zeolites [3], and mesoporous silica
is highly valuable [4, 5]. Among the several nanoreactors, mesoporous silica com-
pounds, mainly SBA-15, have been extensively considered due to the high surface
spaces, highly well-arranged structure, mechanical constancy, thick walls, and inert
environment for the immobilization of transition metal nanoparticles [6, 7].
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116
4-020-04218-4) contains supplementary material, which is available to authorized users.
*
*
Fatemeh Mohajer
f.mohajer@alzahra.ac.ir
Ghodsi Mohammadi Ziarani
gmohammadi@alzahra.ac.ir
1
2
Department of Chemistry, Faculty of Physics and Chemistry, University of Alzahra, Tehran,
Iran
School of Chemistry, College of Science, University of Tehran, Tehran, Iran
Vol.:(0123456789)
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F. Mohajer et al.
Jiang and co-workers reported the generation of the 2D metals, such as
mesoporous compounds with many active sites, which act as catalysts. The
mesoporous metallic Ir nanosheets have high electrocatalytic activity in the
oxygen evolution reaction (OER) [8]. In another attempt, palladium-catalyzed
decarbonylative Suzuki–Miyaura of amides applied in the synthesis of biaryls
through the activation of the N–C(O) amide bond [9–11].
The application of several nanoporous metals such as Cu, Ru, Rh, Pd, Pt, and
Au under diferent conditions through electrochemical deposition was exten-
sively increased in diferent reactions [12, 13]. Application of the metal nano-
particles in catalysis, particularly in organic moieties, has received much atten-
tion [14, 15]. As a result, palladium nanoparticles (Pd NPs) have received much
consideration [16]. In this study, Pd NPs sustained on the two-dimensional hex-
agonal structures of SBA-15 to avoid accumulation [17]. The mesoporous struc-
ture of SBA-15 is full of silanol groups; this hydrophilic structure decreased the
transportation of hydrophobic compounds. However, hybrid porous scafolds of
SBA-15 with ligands containing organic groups aforded the hydrophobic and
hydrothermally steady structures to apply in organic synthesis [18, 19].
Suzuki–Miyaura is a coupling reaction to produce the biaryl compounds in
the presence of the diferent catalysts, including Pd [20]. There are numerous
kinds of Pd-attached ligand-based SBA-15, which were reported for the synthe-
sis of biaryl compounds [2, 21–23]. Cao and co-workers designated the com-
bination of a Pd-diimine@SBA-15 catalyst for the Suzuki–Miyaura coupling
by immobilizing Pd ions and diimine-functionalized SBA-15 mesoporous [24],
then in another attempt Sarkar and co-workers organized an SBA-15 functional-
ized by thiol in the presence of the Pd catalyst for Suzuki–Miyaura coupling
reaction [25]. Ghorbani-Vaghei et al. designated the synthesis of the SBA-15/
AO/Pd(II) nanocatalyst by grafting of the amidoxime group on SBA-15 silica in
the presence of the PdCl2 [26].
Carbon–carbon (Csp2–Csp2) bond-creating cross-coupling reactions used to
give symmetrical and unsymmetrical compounds, which were used in several
one-pot methods [27]. Also, it is clear that the Suzuki–Miyaura coupling reac-
tion of aryl halides with aryl boronic acids is a practical approach to the synthe-
sis of biaryl structures [9–11, 28]. Since the Pd-based homogeneous catalysis
caused problems in the separation of the expensive palladium catalyst from the
produced compounds [29], immobilization of Pd catalyst solved this problem to
respect the green environment [30]. Thus, in the subject of palladium chemistry,
the study of useful and recyclable catalysts is an important issue.
Also, inexpensive and environmentally benign heterogeneous catalytic com-
plexes are striking development, which is essential in this subject. The abun-
dant eforts have been dedicated to the growth of efcient and selective cata-
lyst to be applied in the Suzuki–Miyaura coupling reaction [31, 32]. In this
study, the functionalized SBA-15 compound has been used as the most common
supports, which was developed the surface and stability of the catalyst in the
Suzuki–Miyaura coupling reaction [33].
1 3

The synthesis of SBA-Pr-3AP@Pd and its application as a highly…
Results and discussion
Synthesis of SBA‑Pr‑Cl
In this process, SBA-15 was prepared according to the literature [34].
Synthesis of SBA‑Pr‑3AP
The 2,4,6-triaminpyrimidine compound (0.25 g) was added to the dispersed SBA-
Pr-Cl (1 g) in EtOH, and Et3N refuxed for 24 h. The obtained white powder was
fltered and washed with excess EtOH, to remove any residual organosilane by
soxhlation method using EtOH as solvent over a 24 h to obtain SBA-Pr-3AP as
the white powder, which was dried at ambient temperature.
Immobilization of Pd(II) ions on surface of SBA‑Pr‑3AP@Pd
SBA-Pr-3AP (1.0 g) and palladium chloride (0.2 g) in EtOH (40 mL) was refuxed
for 24 h. The dark gray powder as a resulting solid was fltered, washed with ace-
tone, and dried in vacuum at 80 °C for 2 h to give SBA-Pr-3AP@Pd. According
to the AAS, 25.91 wt % of palladium was precipitated on the synthesized catalyst.
Also, there is no Pd in the reaction solution until the 7th run.
Suzuki–Miyaura cross‑coupling reaction
The mixture of various aryl halides (1 mmol), phenylboronic acid (1.3 mmol) and
K2CO3 (2 mmol) was stirred at the round-bottom fask in the presence of SBA-
Pr-3AP@Pd catalyst (0.002 g) in H2O: EtOH (4 mL) under an air atmosphere at
100 °C. The reaction progress was checked by thin-layer chromatography (TLC).
At the end of the reaction, the SBA-Pr-3AP@Pd catalyst was fltered of, and the
mixture was cooled down to ambient temperature. Next, the organic layer was
extracted with chloroform and water. The resulting residue was purifed by plate
chromatography using n-hexane and ethyl acetate as eluents. The chemical struc-
ture of the desired products was confrmed by melting point and GC–MS analysis.
Characterization and synthesis of catalyst
In the frst step, SBA-15 reacted with (3-chloropropyl)triethoxysilane in dry
toluene under refux condition to form SBA-Pr-Cl [35], which reacted with the
2,4,6-triamino pyrimidine in EtOH using Et3N as a base under refux condition to
give SBA-Pr-3AP. In the last step, the Pd ions were immobilized on the nanohet-
erogeneous surface catalyst of SBA-Pr-3AP (Scheme 1), which was characterized
by XRD, SEM, FT-IR, N2 adsorption–desorption, EDX, and TGA analysis. The
1 3

F. Mohajer et al.
Scheme 1 The synthetic procedure for the preparation of SBA-Pr-3AP@Pd catalyst
immobilized palladium catalyst was used in the Suzuki–Miyaura cross-coupling
reaction as an efcient catalyst [36].
FT‑IR analysis
To characterize and confrm the functionalized groups on the catalyst, FT-IR spec-
troscopy was applied, as shown in Fig. 1 for (a) SBA-15 (b) SBA-Pr-Cl, (c) SBA-
Pr-3AP and (d) SBA-Pr-3AP@Pd. The bands at 800, 960, and 1100 cm−1, are
Fig. 1 FT-IR spectra of a SBA-15, b SBA-Pr–Cl c SBA-Pr-3AP d SBA-Pr-3AP@Pd
1 3

The synthesis of SBA-Pr-3AP@Pd and its application as a highly…
existing in all spectra, which are related to Si–O–Si symmetrical stretching vibra-
tions, Si–OH symmetrical stretching vibrations, and unsymmetrical stretching vibra-
tions of Si–O–Si spectroscopy, respectively. In the SBA-Pr-Cl (b), SBA-Pr-3AP (c),
and SBA-Pr-3AP@Pd (d), the peaks appearing at 2852 and 2956 cm−1 are the rep-
resentative of aliphatic CH2 groups, which demonstrates the propyl group into the
pore walls of SBA-15. The peak around 600-800 cm−1 shows Cl group in the second
spectrum. The stretching vibration of the carbon–carbon double bond in aromatic
ring appeared at 1554 cm−1, and the peaks of 1454 cm−1 displayed stretching vibra-
tions of the C=N group for the spectra of (c) and (d). The band at 1648 cm−1 is
due to the imine bond of the aromatic ring and its stretching vibrations displayed
at 705 cm−1. Moreover, the band at 578 cm−1 in the spectrum of SBA-Pr-3AP@Pd
is assigned to stretching of Pd–N [37]. These results showed that the synthesized
SBA-15 was efectively functionalized with Pd species and obtained the fnal cata-
lyst SBA-Pr-3AP@Pd.
EDX analysis
The EDX spectrum in Fig. 2 explains the presence of the elements C, N, O, Si, and
Pd in SBA-Pr-3AP@Pd. The palladium peak displays the immobilization of the Pd
nanoparticles on the surface of SBA-Pr-3AP@Pd.
BET analysis
The nitrogen adsorption–desorption isotherms and the BJH pore size distribution
(based on the adsorption branch of the isotherms) for all samples SBA-15, SBA-
Pr-3AP, and SBA-Pr-3AP@Pd are shown in Figs. 3 and 4. Type IV characterizes
the isotherms with an H1-type hysteresis loop defned by IUPAC, demonstrating
Fig. 2 EDX Spectrum of SBA-Pr-3AP@Pd
1 3

F. Mohajer et al.
Fig. 3 N2 adsorption–desorption
isotherms of a SBA-15, b SBA-
Pr-3AP, c SBA-Pr-3AP@Pd
Fig. 4 BJH pore size distribution curves of a SBA-15, b SBA-Pr-3AP, c SBA-Pr-3AP@Pd
Table 1 Texture properties of a
SBA-15, b SBA-Pr–Cl c SBA-
Pr-3AP d SBA-Pr-3AP@Pd
Entry Catalyst
SaBET (m2g−1
)
Va (cm3g−1
)
DaBJH (nm)
1
3
4
SBA-15
SBA-Pr-3AP
SBA-Pr-3AP@Pd 351
898
521
0.99
0.79
0.49
9.9
7.4
5.2
aSBET is a specifc surface area, V total pore volume, and DBJH aver-
age pore diameter
1 3

The synthesis of SBA-Pr-3AP@Pd and its application as a highly…
the well-ordered mesoporous arrangement of SBA-15. Table 1 presents the
results for three structural parameters of the samples, including specifc surface
area (BET method), total pore volume, and pore diameter (BJH method). Suc-
cessful incorporation of functional organic materials into mesoporous SBA-15
silica pores and the inclusion of Pd into this structure shifted the pore size to a
smaller value and led to diminishing in pore volume and surface area.
XRD analysis
Low-angle XRD patterns of SBA-15 and SBA-Pr-3AP@Pd catalyst are shown in
Fig. 5. SBA-15 has a strong difraction refection (100) and two small difraction
refections (110) and (200) due to hexagonal symmetry and its long-range order-
ing structure [38]. The SBA-Pr-3AP@Pd marks a decrease in the overall intensity
of the (100), (110), and (200), which might be related to the organic compounds
and Pd-attached particles.
There is a fat pattern in the wide-angle XRD difraction pattern, which is
related to the pure SBA-15 and SBA-Pr-3AP. Two peaks around 40° and 45°
could be attributed respectively to the (111) and (200), which are related to the
metallic Pd(II), the fresh SBA-Pr-3AP@Pd catalyst difractogram. It was proved
that the Pd(II) was immobilized on the SBA-Pr-3AP (Fig. 6).
100
110
200
a
b
2Ө (°)
Fig. 5 Low-angle XRD patterns of a SBA-15, b SBA-Pr-3AP@Pd
1 3

F. Mohajer et al.
(a): SBA-15-Pr-3AP
(b): SBA-15-Pr-3AP@Pd
2ϴ (degree)
Fig. 6 The wide angle XRD patterns of a SBA-Pr-3AP, b SBA-Pr-3AP@Pd
Fig. 7 SEM images of a SBA-Pr–Cl, b SBA-Pr-3AP, c SBA-Pr-3AP@Pd
SEM analysis
A typical scanning electronic microscopy (SEM) images of SBA-15 (a), SBA-
Pr-3AP (b), and SBA-Pr-3AP@Pd (c) was not changed as shown in Fig. 7. In
this case, the arrays of two-dimensional hexagonal mesoporous SBA-15 and the
attachment of organic components inside the pore channels of SBA-15 silica has
no distinct infuence on the morphology of composition.
To approve the synthesized SBA-Pr-3AP@Pd catalyst nature, its TEM image
was recorded after reaction completion, which showed the presence of Pd nano-
particles, as shown in Fig. 8.
1 3

The synthesis of SBA-Pr-3AP@Pd and its application as a highly…
Fig. 8 TEM images SBA-Pr-3AP@Pd
TGA analysis
The thermal stability of the synthesized SBA was examined by thermogravimetric
analysis. The TGA thermograms for the SBA-Pr-3AP and SBA-Pr-3AP@Pd dis-
plays the frst weight loss below 200 °C, and this could be related to the desorption
of physically adsorbed water (Fig. 9). The apparent mass change (18%) from 200 to
790 °C is probably due to the decomposition of organic groups. Moreover, relatively
slow weight loss at elevated temperatures could be related to the dehydration of the
surface –OH groups. So, the TGA curves confrm the successful grafting of organic
groups onto the surface of silica.
The evaluation of the synthesized catalyst SBA-Pr-3AP@Pd was efected by its
catalytic activities in the Suzuki–Miyaura cross-coupling reaction. Several param-
eters, such as solvent (EtOH, water, and toluene), the base quantity, and the catalyst
amount, were optimized to fnd the best reaction conditions. The Suzuki–Miyaura
coupling reaction model of 4-iodobenzene and phenylboronic acid under mild con-
ditions with a little amount of Pd was designated as a typical reaction.
As shown in Table 2, the best result was obtained when the reaction was car-
ried out in the presence of SBA-Pr-3AP@Pd in H2O:EtOH as solvent using
105
100
18%
%18
95
90
85
80
75
70
65
60
a
b
23%
c
SBA-Pr-Cl
SBA-Pr-3AP
SBA-Pr-3AP-Pd
0
200
400
600
800
1000
Temperature (°C)
Fig. 9 TGA curves of a SBA-Pr–Cl, b SBA-Pr-3AP, c SBA-Pr-3AP@Pd
1 3

F. Mohajer et al.
Table 2 Optimization of the
Entry Base
Solvent
Temp. (°C) Pd (mol %) Yield (%)b
reaction conditions
1
2
3
5
6
7
8
9
10
11
12
13
14
15
16
17
K2CO3 Toluene
K2CO3 DMF
K2CO3 DMSO
K2CO3 EtOH
K2CO3 Neat
120
120
120
120
120
120
120
120
120
110
100
90
0.10
0.10
0.10
0.10
0.10
0.10
0.10
0.10
0.10
0.10
0.10
0.10
–
17
74
71
26
Trace
–
19
80
83
91
93
92
–
–
Et3N
DMF
DMF
NaOH DMF
KOH
KOH
KOH
KOH
KOH
KOH
DMF
DMF
DMF
DMF
DMF
DMF
100
100
0.05
0.002
0.07
96
96
96
K2CO3 H2O:EtOH 120
KOH DMF 100
aReaction conditions: 4-iodobenzen (1.0 mmol), phenylboronic acid
(1.3 mmol), K2CO3 (2 mmol), SBA-Pr-3AP@Pd catalyst (0.002 g),
base (2 mmol) and solvent (4 mL)
Scheme 2 The Suzuki–Miyaura cross-coupling reaction in the presence of SBA-Pr-3AP@Pd catalyst
K2CO3 as a base at 100 °C. With the optimized conditions, the reaction was con-
tinued and completed (Scheme 2, Table 3). Various aromatic aryl halides with
phenylboronic acid were reacted in the presence of the SBA-Pr-3AP@Pd as a cat-
alyst and H2O/EtOH as a solvent. It is important to mention that the time of the
reaction in each of the products determined through TLC.
To display the value of this catalyst in the Suzuki–Miyaura reaction, the
obtained results were compared with previously reported in the literature, as
shown in Table 4, which was compared the reaction between phenylboronic acid
and iodobenzene in the presence of diferent catalysts.
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The synthesis of SBA-Pr-3AP@Pd and its application as a highly…
Table 3 The Suzuki–Miyaura cross-coupling reaction of various aryl phenylboronic acid and aryl halides
in the presence of SBA-Pr-3AP@Pd catalysta
Entry
X
R
Product
Timeb (min)
40
Yieldc (%)
94
mp (°C) [Refs.]
111–114 [2]
1
4-NO2
1-Br
2
3-NO2
1-Br
50
93
111–114 [19]
3
4
4-Cl
1-Br
1-Br
30
40
89
94
212 [2]
Oil [39]
3-Me
5
6
7
8
9
4-Me
4-Br
1-Br
1-Br
I
40
50
15
1 h
40
91
100
96
45–47 [40]
212 [39]
H
71–72 [21]
Oil [15]
4-NH2
4-OMe
Br
I
92
89
89–91 [19]
aReaction conditions: ArX (1.0 mmol), phenylboronic acid (1.3 mmol), K2CO3 (2 mmol), SBA-Pr-
3AP@Pd catalyst (0.002 g), and EtOH:H2O (1:1) (4 mL)
bTime of the reaction detected by TLC
cYield obtained by GC-MS
Table 4 A comparison of
No. Catalyst
Temp. (°C) Time (min) Yield (%)
this work with some reported
procedures
1
2
Pd-SBA-16
70
80
4 h
20
95 [41]
97 [19]
Pd(OAc)2@SBA-
15/PrNHEtNH2
3
4
5
SBA-15/AO/Pd(II)a 50
SBA-15/di-urea/Pd 70
18
20
15
98 [26]
99 [2]
99 This work
SBA-Pr-3AP@Pd
80
aPd immobilized on amidoxime-functionalized Mesoporous SBA-15
The mechanism of the Suzuki–Miyaura cross-coupling reaction in the pres-
ence of SBA-Pr-3AP@Pd was illustrated in Scheme 3, which was described by
the catalytic activity through three steps: oxidative addition, transmetalation, and
reductive elimination [42]. In the oxidative addition step, aryl halides were added
to Pd(0) complex to provide intermediate Ar–Pd(II)–X. In the second step, the
1 3

F. Mohajer et al.
Scheme 3 Mechanism of the Suzuki–Mataura cross-coupling reaction by SBA-Pr-3AP@Pd
aryl boronic acid was activated by a base which treated with aryl palladium (II)
complex through the reductive elimination was aforded the desired product.
Catalyst leaching and recyclability
The catalyst leaching and recyclability were accomplished through the hot fltra-
tion test, to obtain the leaching of Pd from the catalyst during the reaction, for the
Suzuki–Miyaura cross-coupling reaction under the optimal conditions was per-
formed. In this process, after 10 min, the hot reaction mixture was fltered to sep-
arate the catalyst, and the reaction was continued under the supernatant solution.
Through the GC–MS measurements, there is no increase in the product, and there
is no Pd in the fltered solution by AAS (Atomic absorption spectrometry). So, this
result proved that the Pd NPs were frmly grafted on the SBA-Pr-3AP@Pd duo to
the excellent afnity between Pd NPs and 2,4,6-triamino pyrimidine ligand.
Reusability of catalyst
The recyclability of the heterogeneous catalysts is essential from the economic per-
spective. The method of reusing the SBA-Pr-3AP@Pd catalyst was manipulated for
the Suzuki–Miyaura coupling reaction of 4-iodobenzene and phenylboronic acid
upon optimized reaction conditions. After the accomplishment of each cycle, the
solid catalyst was removed from the reaction easily, washed with ethyl acetate and
1 3

The synthesis of SBA-Pr-3AP@Pd and its application as a highly…
70
20
1
2
3
4
Run
5
6
7
Fig. 10 Reusability study on the synthesize of the reaction of the 4-iodobenzene and phenylboronic acid
hot EtOH, after drying through vacuum overnight, then use again in a sequential
run. The results in Fig. 10 determine that the supported catalyst was highly recy-
clable under the studied reaction conditions, preserving almost unaltered catalytic
performance after seven uses.
To investigate the mechanism, the mercury drop test was used, as mercury amal-
gamated the heterogeneous catalyst in contrast with homogenous, [43] a drop of
Hg(0) on the reaction texture of various reactant at refux condition, no catalytic
activity was pictured, which shows that Pd(0) and Pd(II) cycles [44–47].
Conclusion
In conclusion, Pd nanoparticles grafted in SBA-15 to aford active hybrid catalysts
for applying in Suzuki–Miyaura cross-coupling reaction in aqueous media. The
SBA-Pr-3AP@Pd catalyst could be simply removed and recovered from the reaction
mixture. The catalytic activity did not decline even after reusing several times. The
Suzuki–Miyaura coupling reaction was run through phenylboronic acid and various
aryl halides under mild conditions with a little amount of Pd to obtain various diphe-
nyl compounds. This catalyst aforded unique advantages such as excellent product
yields, easy preparation, and short reaction times. Furthermore, the heterogeneous
catalyst was easily recovered by fltration. The main point is that the hybrid catalyst
used at least seven times without any problem. This catalyst could be proposed in
other coupling reactions, such as Sonogashira or Heck.
Acknowledgements We are grateful for the Research Council support of Alzahra University.
Compliance with ethical standards
Conficts of interest The authors declare that they have no confict of interest.
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