Polyacrylamide-g-Reduced Graphene Oxide Supported Pd Nanoparticles as a Highly Efficient Catalyst…
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The reaction system is simple.
The Suzuki–Miyaura cross-coupling reaction is carried
out in low temperature.
in conventional Suzuki coupling reactions usually suffer
from significant loss in the activity due to Pd leaching and
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Organic solvents are not needed.
H2O was used as a green solvent.
Toxic and expensive ligands are not needed.
The yields of the products are very high (due to small
particle size and high dispersion of Pd NPs).
The catalyst can be easily recovered.
Generally, highly dispersed metal NPs on supports with
smaller diameter are known to have higher catalytic activ-
ity due to the advantages of increased low coordination
numbers in NPs and larger surface area, resulting in larger
number of active sites [54]. Therefore, the high catalytic
activity can be attributed to small particle size and high
dispersion of Pd NPs. The size-dependent electronic struc-
tural change may also contribute to increased catalytic
efficiency [55]. On the basis of obtained results, it could
be suggested that the current PAM-g-rGO/Pd is very stable
and efficient catalysts for Suzuki–Miyaura cross-coupling
reactions.
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PAM-g-rGO as a support for Pd NPs is biocompatible.
Acknowledgments We are thankful to the Research Council of the
University of Tehran.
References
The catalytic performance of different Pd-based catalysts
in the coupling of bromobenzene and phenyl boronic acid
are shown in Table 8. The PAM-g-rGO/Pd shows the high-
est performance in comparison to other catalysts. Most of
the other published procedures (Table 8) need long times,
high temperature and use toxic solvents with lower isolated
yields.
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The products of reaction were fully characterized through
melt point, 1H NMR and 13C NMR experiments which were
in accordance with the literatures. The results are as follows:
1
Biphenyl [62]: White solid, mp: 67–70°C. H NMR
(300 MHz, CDCl3, δ in ppm): 7.45 (m, 2H), 7.56 (m, 4H),
7.72 (m, 4H). 13C NMR (75.4 MHz, CDCl3, δ in ppm):
141.2, 128.7, 127.2, and 127.1.
4-Nitrobiphenyl [63]: Brown solid, mp: 111–113°C.
FT-IR (cm−1): 3055, 2921, 1603, 1521, 1477, 1446, 1341,
1306, 1087, 1012, 845, 741. 1H NMR (400 MHz, CDCl3, δ
in ppm): 7.44 (m, 3H), 7.63 (m, 2H), 7.77 (m, 2H), 8.46 (m,
2H). 13C NMR (75.4 MHz, CDCl3, δ in ppm): 147.9, 147.3,
139.0, 129.5, 129.2, 128.0, 127.7, 124.4.
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In summary, PAM chains were successfully grafted to the
GO surface via redox system. Then, the immobilization of
Pd NPs was carried by reducing Pd(II) salts in the presence
of PAM-g-GO. The formation of Pd NPs on the reduced gra-
phene oxide surface was visually observed with the mixture
change in color to black and it was also confirmed by FT-IR,
TEM and X-ray analyses measurements. The PAM-g-rGO/
Pd catalysts prepared showed high activity in Suzuki–Miy-
aura coupling reaction carried out in water under in aero-
bic condition. Recovery and reusability of the supported
catalyst were achieved without significant loss of catalytic
activity and low leaching of Pd. Generally, compared with
literature examples of the Suzuki–Miyaura cross-coupling
reaction, the notable features of our nanocatalyst are:
1 3