Palladium nanoparticles immobilized over Strawberry fruit extract coated Fe3O4 NPs: A magnetic reusable nanocatalyst for Suzuki-Miyaura coupling reactions

Article abstract of DOI:10.1002/aoc.5653

This paper develops a green method for in situ decorated of palladium nanoparticles over Fe₃O₄ nanoparticles, by utilizing Strawberry fruit extract and ultrasound irradiations, with no use of any toxic reducing agent. The structure's characterization is represented via diverse analytical methods such as FT-IR, FE-SEM, TEM, WDX, ICP, EDS and XXPS. Catalytic efficiency of magnetic Fe₃O₄@Strawberry/Pd nanocatalyst is investigated in production of different biphenyls with good turnover frequencies (TOF) and turnover numbers (TON) through Suzuki coupling reactions. Furthermore, the catalyst could be recovered and reused 7 runs without considerable palladium leaching or alteration in its performance.

Full text of DOI:10.1002/aoc.5653

Received: 14 November 2019
DOI: 10.1002/aoc.5653
Revised: 10 December 2019
Accepted: 15 December 2019
F U L L P A P E R
Palladium nanoparticles immobilized over Strawberry fruit
extract coated Fe3O4 NPs: A magnetic reusable nanocatalyst
for Suzuki-Miyaura coupling reactions
Saba Hemmati1
| Mohammad Yousefi2 | Mirmehdi Hashemi Salehi3
|
Mahdis Amiri4 | Malak Hekmati3
1Department of Chemistry, Payame Noor
This paper develops a green method for in situ decorated of palladium
nanoparticles over Fe3O4 nanoparticles, by utilizing Strawberry fruit extract
and ultrasound irradiations, with no use of any toxic reducing agent. The
structure's characterization is represented via diverse analytical methods such
as FT-IR, FE-SEM, TEM, WDX, ICP, EDS and XXPS. Catalytic efficiency of
magnetic Fe3O4@Strawberry/Pd nanocatalyst is investigated in production of
different biphenyls with good turnover frequencies (TOF) and turnover
numbers (TON) through Suzuki coupling reactions. Furthermore, the catalyst
could be recovered and reused 7 runs without considerable palladium leaching
or alteration in its performance.
University, Tehran, Iran
2Department of Chemistry, Yadegar-e-
Imam Khomeini (RAH) Shahr-e-Rey
Branch, Islamic Azad University, Tehran,
Iran
3Department of Organic Chemistry,
Faculty of Pharmaceutical Chemistry,
Tehran Medical Sciences, Islamic Azad
University, Tehran, Iran
4Department of Applied Chemistry,
Faculty of Pharmaceutical Chemistry,
Tehran Medical Sciences, Islamic Azad
University, Tehran, Iran
K E Y W O R D S
Correspondence
biphenyl, magnetic, palladium, Suzuki, ultrasound
Saba Hemmati, Department of Chemistry,
Payame Noor University, Tehran, Iran.
Email: s_organo2007@yahoo.com
Mohammad Yousefi, Department of
Chemistry, Yadegar-e-Imam Khomeini
(RAH) Shahr-e-Rey Branch, Islamic Azad
University, Tehran, Iran.
Email: myousefi50@hotmail.com
1 | INTRODUCTION
Palladium catalyzed cross coupling reactions like
Heck,[22,23] Sonogashira,[24,25] Stille,[26,27] Negishi[28] and
The fabrication of heterogeneous catalysts has been
widely investigated unlike the homogeneous counter-
parts, in terms of the simple work-up, recyclability and
simple of handling.[1–5] Among of heterogeneous
catalysts, many attentions have been paid to magnetite
nanoparticles (MNPs) because of their low cost, stability,
toxicity, good biocompatibility, high reactivity, simple
isolation by an external magnet, and especially, the small
size, large surface area, and suitable magnetic
permeability.[6–21]
Kumada,[29] which are crucial and straightforward
approaches to utilize for producing several valuable
product like natural products, agrochemicals, drugs,
and biologically active compounds. Amongst these
reactions, one of the most significant and greatly used
reactions is Suzuki cross coupling because it contains
several advantages including simple operation, easy
accessibility, excellent functional group tolerance, and
the green nature of the starting products.[30,31] Conse-
quently, there are noticeable effort in recent years, to
Appl Organomet Chem. 2020;e5653.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5653

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HEMMATI ET AL.
make highly efficiently homogeneous or heterogeneous
palladium catalysts by utilizing the Suzuki reac-
tions.[32,33] Although, homogenous catalysts show the
outstanding catalytic performance, some scientists have
been preferred heterogeneous catalysts to homogenous
ones, as it present some benefits such as easy recovery
of catalyst from reaction solution, facile recycling and
requires less labor.[34,35] These benefits enrich it to
utilize the catalysts for useful and practical industrial
applications. Thus, diverse heterogeneous catalytic
systems are developed with several supports like silica,
carbon and clay derivatives with immobilization of Pd
ions.[36–38]
2 | EXPERIMENTAL DESIGN
2.1 | Preparation of the Strawberry fruit
extract
The fresh fruits were rinsed 3 times with DI-H2O, dried
in dark/light conditions and powdered for extraction.
Next, 2 g fruits were combined with 100 ml double-
distilled H2O and boiled for 30 min. Next, the mixture
was cooled to ambient temperature and passed through a
filter paper (Whatman No. 1) to isolate the leaves. The
achieved extract was immediately used to the following
stage.
Based on the research carried out by,[39] this
research develops in situ functionalization of palladium
nanoparticles over surface of magnetic nanoparticles
that are coated by a shell of Strawberry fruit extract
under ultrasonic conditions. The biomolecules of
extract coating on the surface of the Fe3O4 NPs play
role as an eco-friendly reducing agent to decrease Pd
precursor in situ and to stabilize the synthesized Pd
NPs, attaining well distributed Pd/Fe3O4 NPs hybrid
catalyst. The synthesized catalyst NPs are utilized to
prepare biphenyls through Suzuki-Miyaura coupling
(Scheme 1). Moreover, the developed nanocatalyst can
be recycled at least 7 times with no change in their
performance.
2.2 | Fabrication of Pd/Fe3O4
nanocatalyst
At first, Fe3O4 NPs (500 mg) was dispersed in 100 ml
water and sonicated for 20 min at 60 ꢀC. Then, the
Strawberry fruit extract was poured into the mix. Next,
the resulted mix was sonicated again at same tempera-
ture for 30 min, and then, an aqueous solution con-
taining Na2PdCl4 was slowly poured into the reaction
solution (0.04 g, 50 ml, the drip rate was 1 ml/min) using
dropping funnel under sonication. Then, the reaction
mixture was agitated for another 20 min using ultrasonic.
SCHEME 1 Pathway preparation of
Pd/Fe3O4 NPs. mediated by Strawberry fruit
extract under ultrasonic irradiations

HEMMATI ET AL.
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Next, the resulted mixture was cooled to ambient temper-
ature and MNPs of Pd/Fe3O4 NPs were separated from
the solution as a dark solid using a magnet and rinsed
several times with H2O and EtOH. The obtained
nanocatalyst was dried. The amount of Pd was
0.21 mmol.g−1, which was measured using ICP.
2.3 | General procedure for the Suzuki-
Miyaura reactions
1.0 mmol of Ar-X, 1.0 mmol of Ph-B(OH)2, 2 mmol of
K2CO3 and 44 mg of Pd/Fe3O4 NPs (0.1 mol %) were
poured to 5 ml of H2O-EtOH (1:1, v/v) and agitated at
ambient temperature for optimal time (Table 2). After
completing the reaction (controlled with TLC), the reac-
tion mix was diluted with ethylacetate (5 ml), and the
catalyst was isolated using a suitable magnet. Organic
phase comprising biphenyl compounds, was removed
and related biphenyls were achieved through evaporation
of the solvent.
FIGURE 1 FTIR spectrum of a) Fe3O4, b) Strawberry fruit
extract, and c) Pd/Fe3O4 NPs
3 | RESULTS AND DISCUSSION
biomolecules such as polyols and flavonoids in the
extract. In the spectra of Pd/Fe3O4 NPs (Figure 1c), with
appearance of stretching vibration of the Fe-O in 563 and
632 cm−1, there are several extra bands in the spectrum
belonging to the extract coating. Absorption peaks
appeared at 1613 and 1072 cm−1 belong to stretching
vibrations of C=O and C-O, respectively.[40] Bands
observed at 2921 and 2861 cm−1 are characteristic of C-H
stretching vibrations.[41] The bands appeared at
~1400–1600 cm−1 can be assigned to stretching C=C aro-
matics ring vibrations.[42] The existence of these bands
shows the hydrophilic features of the NPs. FT-IR analyses
show that Strawberry fruit extract is effectively coated on
the surface of Fe3O4 NPs. Furthermore, the phenolic
hydroxyl groups of flavonoids and other phenolic com-
pounds present in the extract is responsible for the
bioreduction of the Pd2+ ions to Pd0 and stabilization of
Pd NPs.[43]
FE-SEM is an important tool to survey some items
such as the shape of particle, distribution of size and mor-
phology of surface. The FE-SEM images of Pd/Fe3O4 NPs
(Figure 2) was revealed that the nanocatalyst in
nanometer-sized particles with quasi-spherical shape. In
addition, the in situ decreased and its immobilized Pd
NPs on Fe3O4 surface could be verified using its EDX
analysis. The EDX confirmed the existence of extract
shell and palladium species on the surface of Fe3O4 NPs
that the results verified the existence of Fe, C, O, and Pd
in Figure 3. The existence of the Pd signals in the
Based on Scheme 1, the Fe3O4 NPs were first coated by
extract of Strawberry fruit to immobilizing the Pd NPs on
the surface of MNPs through ultrasound-assisted conden-
sation. In the following phase, the interaction between
the Pd2+ ions and the hydroxyl groups of the extract's bio-
molecules resulted successful connection of the ions to
the extract coated MNPs. The reduction of Pd2+ ions to
Pd0 occurred in the existence of ultrasound waves by
decreasing biomolecules of extract. The Pd of the
nanocatalyst was 0.21 mmol g−1. The structural features
of the Pd/Fe3O4 NPs were investigated by several analyti-
cal methods such as FT-IR, FESEM, EDS, TEM, ICP and
XPS analysis.
To evaluate the chemical structural variations from
Fe3O4 NPs to Pd/Fe3O4 NPs, we accomplished FT-IR
spectroscopic analysis. Figure 1 shows FT-IR spectra of
Fe3O4 NPs, Strawberry fruit extract, and Pd/Fe3O4 NPs.
In the spectra of Fe3O4 NPs (Figure 1a), the broad peak
at 1619 and 3420 cm−1 are related with the surface-
adsorbed water and hydroxyl groups of Fe3O4 NPs,
respectively, however, the bands at 440 and 560 cm−1 are
assigned to the Fe-O bonds. Moreover, the band appeared
at 630 cm−1 shows the presence of Fe3O4 structure and
reveals no presence of impurity. The IR spectra of the
aqueous extracts of Strawberry fruit demonstrated bands
at 3447 (OH), 2925 (C-H), 1638 (CO), 1400–2600(C=C),
1280 (C-O), 1061 (C-O-C), and 860 cm−1 (O-H)
(Figure 1b). These absorptions indicated the existence of

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HEMMATI ET AL.
FIGURE 5 TEM image of the as-prepared Pd/Fe3O4 NPs
FIGURE 2 FESEM image of Pd/Fe3O4 NPs
with random distribution. Further the Pd nanoparticles
(black dots) are of lower size than nano crystalline Fe3O4
NPs. Moreover, the existence of the extract layer acted for
in situ reduction and immobilization of Pd over the sur-
face of Fe3O4/extract NPs.
The XPS analysis is implemented because it is an
effective tool to explore the electronic properties of spe-
cies. Figure
6
shows the elemental XPS scans
corresponding to the Pd/Fe3O4 NPs in the Fe 2p, C 1 s
and Pd 3d regions. This figure obviously shows the bands
correlated to carbon, palladium and iron. Besides, the
two binding energy bands of 335.42 and 341.35 eV in the
Pd 3d region, which related to Pd 3d3/2 and Pd 3d5/2
,
respectively.[32,44] This results confirmed that the extract
shell reduced all adsorbed Pd (II) ions to Pd(0) atoms.
Here, it should be mentioned that the presence of the bio-
molecules in the Pd/Fe3O4 NPs is re-proved by the exis-
tence of C1s in the XPS spectrum.
The assessment of catalytic activity of the Pd/Fe3O4
NPs was carried out using Suzuki coupling reaction. To
generate a more effective catalytic procedure, the factors
like the influence of the solvent, type of base and the
amount of nanocatalyst were investigated. This reaction
was executed at room temperature for reaction of phenyl
boronic acid with bromobenzene as model reaction (see
FIGURE 3 EDX data for Pd/Fe3O4 NPs
nanocatalyst,s EDX provided the successful production of
Pd/Fe3O4 NPs. Furthermore, the existence of C, Fe and
Pd was emphasized on elemental mapping images. To
better understand, Figure 4 illustrates that Pd is dispersed
uniformly on the Fe3O4 NPs surface.
The morphological properties of the Pd/Fe3O4 NPs
were also controlled using TEM. The outcome is shown
in Figure 5. It detectable that the Pd/Fe3O4 NPs
nanoparticles are crystalline, having size below 20 nm
FIGURE 4 Elemental mapping of
Pd/Fe3O4 NPs shows the presence of Fe, C, and
Pd atoms in the nanocomposite

HEMMATI ET AL.
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FIGURE 6 XPS spectrum related to the
scan of Pd/Fe3O4 NPs in the Fe 2p, C 1 s and Pd
3d regions
Table 1 for more details). Diverse solvents were analyzed
and then H2O/ethanol (1:1) was chosen as the best sol-
vent. In addition, the kind of the base was studied, based
on which it was found that K2CO3 is the most effective
base. The reaction was surveyed without applying cata-
lyst and as expected, the desired product was not
achieved. (as can be seen from Table 1, entry 10) and it
was reported that the presence of catalyst was crucial for
occurring the reaction. It was observed that 0.1% mol of
the Pd catalyst is adequate to perform the reaction under
the optimal conditions. (Table 1, entry 7). Under the opti-
mal conditions, various kinds of aryl halides (X = I, Br,
Cl) were utilized to couple with Ph-B(OH)2 (Table 2,
entries 1–15). The aryl halides with an electron-donating
substitute in the para-position show less performance
comparing to those have an electron-withdrawing substi-
tute. Besides, to evaluate catalytic performance of the
synthesized nanocatalyst, several deactivated and acti-
vated aryl chlorides were taken into account. According
to the acquired outcomes, moderate performances were
attained under optimized condition (Table 2, entries 3, 6
and 9), as the bond energy of C–Cl is more than C-Br,
coupling yield of aryl chloride was smaller than that of
aryl bromide (Table 2, entries 3, 6 and 9). The
corresponding product for iodo- and bromo-benzenes
were obtained exclusively with good turnover frequencies
(TOF) and turnover numbers (TON).
The reusability of the catalyst system is one of the
main points from the standpoint of cost-effectiveness and
environmental impact. As such, the recovery and recycla-
bility of the Pd/Fe3O4 NPs was assessed using the Suzuki
C-C coupling reaction of phenyl boronic acid with
4-bromotoluene under same conditions. The Pd/Fe3O4
NPs catalyst exhibited high performance and recyclability
of at least 6 times, with minor fluctuation in yields
(Figure 7). In the subsequent cycles, the yields decreased
due to losing concentration of catalyst in each recovering
procedure. Furthermore, ICP analysis on the recycled
catalyst confirmed an insignificant alteration in their Pd
level (from 0.21 to 0.20 mmol/g), which shows a legible
palladium leaching over the following reaction runs.
Consequently, it can be stated that the Pd/Fe3O4 NPs are
practically recyclable.
As the last experiment, heterogeneity of the
nanocatalyst was investigated for the Suzuki reaction by
implementing hot filtration on the coupling reaction of
TABLE 1
Optimization of the reaction conditions in Suzuki-Miyaura coupling reaction of bromobenzene with phenyl boronic acida
Entry
Pd (mol%)
0.10
Solvent
Base
Time (min)
Yield (%)b
1
Toluene
K2CO3
K2CO3
K2CO3
K2CO3
Et3N
120
120
120
120
90
70
75
2
0.10
DMF
3
0.10
EtOH
50
4
0.10
H2O
60
5
0.10
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
EtOH/H2O
70
6
0.10
NaOAc
K2CO3
K2CO3
K2CO3
K2CO3
No base
90
85
7
0.10
60
96
8
0.05
90
75
9
0.20
60
96
10
11
0.0
120
120
0
0.10
Trace
aReaction conditions: bromobenzene (1.0 mmol), phenylboronic acid (1.0 mmol), catalyst, base (2 mmol), solvent (3 ml) and 25 ꢀC.
bIsolated yield.

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HEMMATI ET AL.
TABLE 2
Suzuki–Miyaura coupling reaction of different aryl halides with phenyl boronic acida
Entry
RC6H4X
H
X
I
Time (min)
Yield (%)b
TONc
960
960
500
960
920
450
900
900
400
950
900
900
800
920
900
TOFd
1920
960
1
30
96
96
50
96
92
45
90
90
40
95
90
90
80
92
90
2
H
Br
Cl
I
60
3
H
24 (hr)
45
20.8
1280
460
4
4-CH3
4-CH3
4-CH3
4-COCH3
4-COCH3
4-COCH3
4-OCH3
4-OCH3
4-NO2
4-NO2
4-F
5
Br
Cl
I
120
24 (hr)
45
6
18.7
1200
450
7
8
Br
Cl
I
120
24 (hr)
60
9
16.6
950
10
11
12
13
14
15
Br
I
120
90
450
600
Br
I
120
60
400
920
4-F
Br
120
450
aReactions were performed under aerobic conditions (air) in 3 ml of H2O/EtOH (1:1), 1.0 mmol arylhalide, 1.0 mmol phenylboronic acid and
2 mmol K2CO3 in presence of the c catalyst (0.1 mol% of Pd) at 25 ꢀC.
bIsolated yield.
cTON, turnover numbers (TON = Yield/Amount of catalyst (mol).
dTOF, turnover frequencies (TOF = (Yield/Time)/Amount of catalyst (mol).
FIGURE 7 The recycling of the Pd/Fe3O4 NPs
FIGURE 8 TEM image for recycled Pd/Fe3O4 NPs
model substrates under same conditions. Following
30 min reaction time, when 65% yield was achieved, the
nanocatalyst was eliminated from the mixture using an
external magnet and the procedure was controlled for
another 30 min. No development was recognized in the
yield. Thus, this result shows heterogeneity of the cata-
lyst. The TEM image (Figure 8) of the catalyst after the
6 runs indicated the preservation of the catalyst's
nanostructure.
Furthermore, we checked the catalytic superiority
and remarkable features of Pd/Fe3O4 NPs in comparison
to other catalytic systems reported in the literature for
Suzuki-Miyaura coupling reaction (Table 3). Obviously,
the Pd/Fe3O4 NPs provided higher yields in a shorter
reaction time and higher catalytic performance for C-C
coupling reaction, as compared to other catalysts.

HEMMATI ET AL.
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TABLE 3
Catalytic performance of different catalysts in the coupling reaction of iodobenzene and bromobenzene with phenylbronic
acid
Entry
Catalyst (mol%)
Conditions
X
Time (hr)
2.0
Yield (%)
78, 65
98, 90
95, 88
77.7
Refs.
[45]
1
2
3
4
5
6
7
8
Bis (oxamato)palladate (II) complex (5)
NHC-Pd (II) complex (0.2)
SiO2-pA-Cyan-Cys-Pd (0.5)
Pd3(dba) (1)
Et3N, n-Bu4NBr, 120 ꢀC
K3PO4.3H2O, H2O, TBAB, 40 ꢀC
K2CO3, H2O, 100 ꢀC
K3PO4, THF, 80 ꢀC
I, Br
I, Br
I, Br
Br
[46]
[47]
[48]
[49]
[50]
[51]
5.0, 6.0
5.0, 5.5
24
Pd–BOX (2)
K2CO3, DMF, 70 ꢀC
I
6.0
100
γ -Fe2O3-acetamidine-Pd (0.12)
Pd-isatin Schiff base-γ-Fe2O3 (0.5, 1.5)
Pd/Fe3O4 NPs (0.1)
Et3N, DMF, 100 ꢀC
I, Br
I, Br
I, Br
0.5, 0.5
0.5, 0.7
0.5, 1.0
96, 96
95, 90
96, 96
Et3N, Solvent-free, 100 ꢀC
K2CO3, H2O-EtOH, 25 ꢀC
this work
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4 | CONCLUSIONS
This paper developed a novel, efficient, and environmen-
tally friendly approach for synthesis of an extremely
active heterogeneous Pd nanocatalyst. The proposed
approach relied on ultrasound-assisted stabilization and
functionalization of Pd NPs on Fe3O4 NPs, which were
coated with a biomolecules of Strawberry fruit extract.
The Suzuki-Miyaura coupling reaction was performed for
a wide range of aryl halides, based on which excellent
yields of the relating products were achieved under opti-
mization conditions. A noteworthy feature of the catalyst
was illustrated to be its recyclability by an external mag-
net, without any palladium leaching. The synthesized
catalyst was reused many times without losing its cata-
lytic activity. The results demonstrated that the adopted
green approach of synthesizing Pd NPs is could be useful
for synthesis of other metal nanoparticles.
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ACKNOWLEDGEMENTS
The authors gratefully acknowledge the financial and
other support of this research, provided by Payame Noor
University (PNU), Tehran Medical Sciences, IslamicAzad
University and Yadegar-e-Imam Khomeini (RAH) Shahr-
e-Rey Branch, Islamic Azad University, Tehran, Iran.
CONFLICT OF INTEREST
There are no conflicts to declare.
ORCID
Saba Hemmati https://orcid.org/0000-0003-2672-7948
Malak Hekmati https://orcid.org/0000-0003-0790-569X
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How to cite this article: Hemmati S, Yousefi M,
Salehi MH, Amiri M, Hekmati M. Palladium
nanoparticles immobilized over Strawberry fruit
extract coated Fe3O4 NPs: A magnetic reusable
nanocatalyst for Suzuki-Miyaura coupling
reactions. Appl Organomet Chem. 2020;e5653.
https://doi.org/10.1002/aoc.5653