Sustainable catalysis using magnetic chicken feathers decorated with Pd(0) for Suzuki-cross coupling reaction

Article abstract of DOI:10.1016/j.tetlet.2015.08.081

Magnetic nanoparticles (Fe₃O₄) coated with chicken feather (CF) were synthesized and subsequently grafted with palladium nanoparticles (Pd NPs) using in situ preparation approach. The synthesized catalyst showed excellent activity for Suzuki cross coupling reaction between aryl halides and phenylboronic acid. After completion of the reaction, the catalyst could conveniently be separated via magnetic separation. More importantly, the presence of amino and carboxyl groups on the surface due to chicken feather, provided sufficient binding sites for Pd NPs, and therefore make the synthesized material highly stable. No leaching was observed during the reaction as ascertained by ICP-AES analysis. Furthermore, the catalytic activity of this supported catalyst did not show any significant loss after being used for at least six times.

Full text of DOI:10.1016/j.tetlet.2015.08.081

Accepted Manuscript
Sustainable catalysis using magnetic chicken feathers decorated with Pd(0) for
Suzuki-cross coupling reaction
P. Padma Latha, Mukesh Bhatt, Suman L. Jain
PII:
S0040-4039(15)30035-6
DOI:
http://dx.doi.org/10.1016/j.tetlet.2015.08.081
TETL 46665
Reference:
Tetrahedron Letters
To appear in:
Received Date:
Revised Date:
Accepted Date:
23 June 2015
18 August 2015
27 August 2015
Please cite this article as: Padma Latha, P., Bhatt, M., Jain, S.L., Sustainable catalysis using magnetic chicken
feathers decorated with Pd(0) for Suzuki-cross coupling reaction, Tetrahedron Letters (2015), doi: http://dx.doi.org/
10.1016/j.tetlet.2015.08.081
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Graphical Abstract
Sustainable catalysis using magnetic chicken feathers decorated
with Pd(0) for Suzuki-cross coupling reaction
Leave this area blank for abstract info.
P. Padma Latha, Mukesh Bhatt and Suman L. Jain*

1
Tetrahedron Letters
journal homepage: www.els evier.com
Sustainable catalysis using magnetic chicken feathers decorated with
Pd(0) for Suzuki-cross coupling reaction
P. Padma Latha,a Mukesh Bhatta and Suman L. Jaina*
aChemical Sciences Division, CSIR-Indian Institute of Petroleum, Mohkampur, Dehradun-248005 (India)
*Tel No. 91-135-2525788; Email: suman@iip.res.in
ARTICLE INFO
ABSTRACT
Article history:
Received
Magnetic nanoparticles (Fe3O4) coated with chicken feather (CF) were synthesized and
subsequently grafted with palladium nanoparticles (Pd NPs) using in situ preparation approach.
The synthesized catalyst showed excellent activity for Suzuki cross coupling reaction between
aryl halides and phenylboronic acid. After completion of the reaction, the catalyst could
conveniently be separated via magnetic separation. More importantly, the presence of amino and
carboxyl groups on the surface due to chicken feather, provided sufficient binding sites for Pd
NPs, and therefore make the synthesized material highly stable. No leaching was observed
during the reaction as ascertained by ICP-AES analysis. Furthermore, the catalytic activity of
this supported catalyst did not show any significant loss after being used for at least six times.
Received in revised form
Accepted
Available online
Keywords:
Biodegradable catalyst
Magnetic separable catalyst
Chicken feather
C-C coupling
2009 Elsevier Ltd. All rights reserved
.
Palladium
Chicken feathers (CF),
a
poultry waste, produced
magnetic nanoparticles to keep their stability is an important
process. In this regard, various strategies including grafting of
or coating with small organic molecules, surfactants,
polymers, and biomolecules, or coating with an inorganic
layer, such as silica, metal oxide etc. have been developed.12-
worldwide 8.5 billion tonnes annually from feather meal
industry.1 In general, these poultry waste are often disposed
by methods like burning in incineration plants, buried in
landfills, or recycled into low quality animal feeds, which are
limited options of disposal. Furthermore, these methods of
disposal generate green house gases which are detrimental to
the environment. Therefore, the utilization of chicken feathers
to develop new materials and products is highly desired not
only to add value to this waste2-7 but also to reduce the
pollution caused by disposal in landfills. In this regard, main
efforts have been made to develop biodegradable
thermoplastics from chicken feathers through graft
polymerization with methyl acrylates.8
15
Owing to the growing environmental and economical
considerations, utilization of readily available, inexpensive
and biodegradable materials as a greener substitute of various
metal and non-metal catalyst supports are gaining particular
interest in recent decades.
Recently, palladium-catalyzed cross coupling reactions
such as Suzuki-Miyaura, Heck coupling of aryl halides has
been considered to be an effective method for the
construction of C-C bonds in the modern chemical
transformations. Although homogeneous palladium catalysts
have been extensively investigated, their practical uses
remained limited due to the non-recycling ability and tedious
separation of catalyst from the products. Thus, the
heterogenization of homogeneous palladium catalysts or
grafting of palladium nanoparticles to solid organic or
inorganic support matrix offers an attractive solution to
overcome these limitations. In this regard, a number of
catalysts supports for grafting of palladium nanoparticles for
constructing C-C bond through cross coupling reactions have
been investigated.16-25
In continuation to our on-going research herein, we report
a simple, cost effective and efficient Fe3O4@/CF-Pd catalyst
synthesized via grafting of Pd(0) nanoparticles to
magnetically separable chicken feather for catalyzing Suzuki
cross coupling reaction (Scheme 1). Importantly, magnetic
core provides convenient separation of the catalyst from the
reaction mixture in quantitative yield without any loss.
In addition Senoz et al.9 synthesized pyrolyzed chicken
feather fibres from a two-step process (215 °C/15 h +
400−450 °C/1 h) and demonstrated to be as adsorbents for
strong H2 adsorption at low pressures and 77 K. Brandelli et
al.10 produced keratinases from diverse microorganisms
including Eucarya, Bacteria, and Archea domains, which
have been used to be promising candidates to degrade keratin
and possess potential applications in agro-industrial,
pharmaceutical and biomedical fields. However, in the area of
catalysis the use of chicken feathers as support matrix to
develop heterogeneous catalysts is rarely been known. Zheng
et al.11 reported
a
hydrogenation of anisole and benzaldehyde.
feather-palladium complex for
Recently, magnetic nanoparticles (MNPs) have been
established to be robust, easily accessible and important
catalyst support which offers an additional advantage of being
magnetic recovery of the catalyst, thereby eliminating the
requirement of catalyst filtration after completion of the
reaction. However, the naked MNPs possess higher chemical
activity and are easily oxidized in air, resulting in loss of
magnetism. Therefore, the surface functionalization of

2
Tetrahedron
Scheme 1: Palladium catalyzed Suzuki cross coupling reaction
Synthesis and characterization of the catalyst
The schematic representation of the catalyst synthesis is
depicted in Scheme 2. The catalyst was prepared by
sonicating magnetic nano-ferrite (Fe3O4) with powdered
chicken feathers (CF) in water for 5 h, followed by the
addition of palladium acetate which subsequently treated with
NaBH4 to get Pd(0) immobilized magnetic chicken feather
Fe3O4@/CF-Pd(0) catalyst in excellent yield.
Figure 1: FTIR spectra of a) CF; b) Fe3O4@CF; c) Fe3O4@CF-Pd(0).
Afterwards, the crystalline structures of Fe3O4@CF and
Fe3O4@CF-Pd(0) were determined by XRD. As displayed in
Figure 2a, chicken feather has amorphous structure, whereas
in Figure 2b additional six characteristic diffraction peaks
(2θ= 30.2ᴼ, 35.6ᴼ, 43.3ᴼ, 53.8ᴼ, 57.3ᴼ and 63ᴼ) corresponding
to the (220), (111), (400), (422), (551) and (440) reflections
of inverse spinal Fe3O4 were in well accordance with the
previous literatures.26 After anchoring the Pd NPs to
Fe3O4@CF, four characteristic diffraction peaks (2θ = 34ᴼ,
40ᴼ, 46ᴼ and 52ᴼ) corresponding to the (311), (111), (200)
and (422) planes for face-centered cubic Pd (0)were observed
(Figure 2c). Additional crystalline phase of Fe3O4 and Pd (0)
in amorphous chicken feather is another conformation. Here,
the diffraction peaks of Pd NPs are very weak due to amount
of Pd NPs is very low relative to the carriers.
Scheme 2: Synthesis of Fe3O4@/CF-Pd(0) catalyst
The FT-IR spectra of CF, Fe3O4@CF and Fe3O4@CF-
Pd(0) were recorded to confirm the chemical modification
during the immobilization process as shown in panels a, b and
c of Figure 1, respectively. In FTIR spectrum of CF (Figure
1a) the absorption peaks at 1647, 1536 and 3423 cm−1 are
attributed to the characteristic absorption bands of the amide I
and amide II and (-NH, -OH) stretching, respectively. The
FTIR spectrum of Fe3O4@CF showed an additional peak at
around 579 cm−1, corresponding to the Fe-O vibrations
(Figure 1b). The peak shifting of bending vibration of amide I
and amide II from 1647 and 1536 cm-1 to 1640 and 1535 cm-1
was most likely due to the interaction of amide groups of
feather with metal nanoparticles (Figure 1b). Moreover, the
band at around 1072 cm−1, corresponding to C-S bond of the
chicken feather (Figure 1a), was found to be significantly
reduced in Fe3O4@CF (Figure 1b) indicating the strong
interaction between sulfur groups and metal NPs. Further
shifting in the characteristic bands of CF and Fe-O bond was
observed in Fe3O4@CF-Pd(0) (Figure 1c). Taking the above
observations into consideration, it can be concluded that the
Fe3O4@CF and Fe3O4@CF-Pd(0) nanoparticles were
successfully obtained along with a strong interaction between
sulfur and amino–group functionalities of the CF with Fe3O4
and Pd NPs.
Figure 2: XRD patterns of: a) CF; b) Fe3O4@CF and c) Fe3O4@CF-Pd(0).
Surface morphology and the presence of palladium in the
synthesized catalyst were further confirmed by transmission
electron microscopy (TEM) analysis. The TEM image of
Fe3O4@CF-Pd(0) revealed the core-shell structure with the
homogeneous distribution of the CF coated MNPs (Figure S1a).
Figure S1b showed diffraction pattern of Fe3O4@CF-Pd(0) having
fcc and bcc structures of Fe3O4, Pd NPs respectively. The size of
the Pd NPs was found to be about 3–10 nm and were successfully
grafted on the surface of Fe3O4@CF with uniform distribution.

3
Furthermore, the appearance of C, O, Fe and Pd in EDX
analysis of synthesized catalyst clearly indicated the presence
of these elements (Figure S1c and S2). Moreover, elemental
mapping of C, Fe, Pd and the combined composition (Figure
S3a-d) clearly indicated the homogeneous distribution of the
palladium nanoparticles in the chicken feather coated
magnetic core. The loading of palladium in the synthesized
catalyst was found to be 0.27 mmol/g determined by
inductively coupled plasma optical emission spectrometry
(ICP-AES).
Table 1: Results of the optimization experiments.a
Entry Catalyst
(mol %)
Base
Temperature
(ᵒC)
Time
(h)
Yield
(%)b
1
2
0.1
0.2
K2CO3
K2CO3
80
80
5
5
58
75
The surface textural properties of the synthesized
materials i.e. Fe3O4@CF, Fe3O4@CF-Pd(0) was determined
by N2 adsorption/desorption as shown in Figure S4. The N2
adsorption/desorption isotherms of the core–shell magnetic
Fe3O4@CF nanoparticles (Figure S4a) showed a smooth
curve, and the BET surface area, BJH pore volume and pore
size was found to be 59.71 m2/g, 0.16 cm3 g-1 and 3-10 nm,
respectively. As expected the significant reduction in N2
adsorption was achieved after the immobilization of Pd NPs
on the surface (Figure S4b). In addition, the measured BET
surface area, BJH pore volume and pore size for Fe3O4@CF-
Pd(0) was found to be 31.93 m2 g-1, 0.1479 cm3 g-1 and 3–18
nm, respectively.
3
4
5
6
7
8
0.5
1.0
0.5
0.5
0.5
0.5
K2CO3
K2CO3
Na2CO3
KOH
80
80
80
80
80
RT
5
5
92
93
81
67
87
20
5
5
Cs2CO3
K2CO3
5
24
9
0.5
0.5
0.5
0.5
0.5
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
50
80
80
80
80
24
24
24
5
26
10c
11d
12e
13
-
-
80, 32f
88g
5
aReaction conditions: bromobenzene (2 mmol), phenylboronic
acid (3 mmol), base (4 mmol) under a nitrogen atmosphere;
bIsolated product; cIn the absence of catalyst; dusing magnetic
chicken feather as catalyst; eusing Pd@Fe3O4 as catalyst; fisolated
yield after three cycles; gEtOH: H2O (4:1) as a solvent .
Catalytic activity of Fe3O4@CF-Pd(0) in the Suzuki–cross coupling
reaction
The catalytic activity of the synthesized Fe3O4@CF-Pd(0)
catalyst was tested in Suzuki–Miyaura cross coupling reaction
by considering bromobenzene and phenylboronic acid as
model substrates. At first the reaction was performed in water
by varying the amount of the catalyst, using K2CO3 as a base
The recyclability, a key issue of heterogeneous catalysts
from both the economical and environmental points of view,
was also checked for the developed Fe3O4@CF-Pd(0) catalyst
using bromobenzene and phenyl boronic acid as model
substrates. After completion of the reaction the catalyst was
readily separated by external magnet as shown in Figure 3,
and the recovered catalyst was reused as such for subsequent
runs under optimized experimental conditions. The recycling
ability of the recovered catalyst was checked for subsequent
six runs (Figure 4). As shown in Figure 4 the catalyst
maintained its activity and provided almost similar product
yield in all cases. These results confirmed that the developed
catalyst was quite stable and could be recycled for several
runs without any significant loss in the catalytic activity. The
ICP-AES analysis of the recovered catalyst revealed that the
Pd content of the recovered catalyst after six cycles (Pd, 0.26
mmol/g) did not change significantly, which implied that the
catalyst was highly stable.
o
at 80 C under nitrogen atmosphere (Table 1, entry 1-4). As
shown the yield of the product was found to be increased with
increasing the catalyst amount, in the range of 0.1 to 1 mol %.
The reaction afforded a yield of 92%, using 0.5 mol % of [Pd]
within 5h. Further increase in catalyst amount showed no
significant enhancement in the yield of the product (entry 4).
Further, we checked the effect of various bases including
K2CO3, Na2CO3, KOH, and Cs2CO3 under described
experimental conditions (Table 1, entry 2, 5-7). Among the
various bases studied, K2CO3 gave maximum yield of the
desired product at 80 oC in 5 h. Furthermore, the reaction was
o
found to be very slow at room temperature, 80 C was found
to be optimum and further increase in temperature beyond 80
oC did not improve the results to any significant extent (Table
1, entry 8-9). In the controlled blank experiments, the reaction
did not occur neither in the absence of palladium nor by using
the magnetically separable CF as catalyst under identical
reaction conditions (Table 1, entry 10-11). Moreover, we
investigated the effect of various solvents such as THF,
CH3CN, and EtOH: H2O (4:1) and water. Among these
solvents, the reaction did not occur in THF and acetonitrile
solvent. However, the reaction was found to be slow in
ethanol-water mixture and gave slightly lower product yield
(88% isolated yield). The maximum activity of the catalyst in
water is most likely due to the possibly strong hydrogen
bonding between water molecules and amino acid chain.
Owing to this bonding the amino acid chain may get stretched
and provide more accessibility of active palladium sites to the
substrate molecules.
Figure 3: Magnetic separation of the catalyst

4
Tetrahedron
Table 2: Investigation of the substrate scope in the presence of
Fe3O4@CF-Pd(0) in the Suzuki–cross coupling reactiona
Entry
R1
R2
Yield
(%)b
92
H
1
2
3
4
5
6
7
8
H
2-CHO
4-NO2
4-OH
89
H
91
90
H
3-CHO
Figure 4: Results of recycling experiments.
4-NH2
4-CH3
4-COCH3
4-OCH3
90
89
H
H
H
H
85
91
In addition, we also tested the Pd NPs immobilized
to magnetic core (Pd@Fe3O4) to establish the effect of CF
coating onto the magnetic nanoparticles (Table 1, entry 12).
As shown in results, the comparison among these two
catalysts clearly indicated the positive effect of CF coating in
the Suzuki cross coupling reaction in terms of both reactivity
and recyclability, in particular to the recyclability issue. The
improved catalytic performance of Fe3O4@CF-Pd(0) is most
likely due to the presence of amino and carboxyl group
functionalities on the surface which efficiently stabilized the
Pd NPs and played a crucial role towards preventing the
leaching of Pd NPs or part of it from the support.
aReaction conditions: substrate (2 mmol), phenylboronic acid
(3 mmol) in the presence of K2CO3 (2 eq), catalyst Fe3O4@CF-
Pd(0) (0.5 mol% of [Pd] in H2O under a nitrogen atmosphere
for 5 h; bIsolated yields.
We have demonstrated the first successful synthesis of
magnetically separable chicken feather grafted with
palladium nanoparticles for catalyzing Suzuki cross coupling
reaction using water as reaction medium. The developed
catalyst was found to be quite stable and could be readily
recovered by external magnet. The catalyst showed consistent
activity for six subsequent runs without showing any
detectable leaching of metal particles. Facile recovery of the
catalyst, use of biodegradable waste such as chicken feather
as support matrix and water as environmentally benign
reaction media make this method green and attractive for
sustainable development of organic synthesis.
Furthermore, to ascertain the catalytic activity originated
from the grafted Pd NPs not from leached Pd, a control
experiment between bromobenzene and phenylboronic acid in
the presence of Fe3O4@CF-Pd(0) was performed to proceed
for 2 h under the optimized conditions providing the desired
cross-coupling product in 32% yield. Subsequently, the
o
catalyst was magnetically separated at 80 C; the remaining
Acknowledgments
reaction solution was stirred again for next 22 h. In this case
the isolated yield of the biphenyl product was remained 32 %
yield, which showed that almost no yield increase had
occurred after removing the immobilized Pd NP catalyst. The
result of the hot magnetic separation experiment confirmed
that the developed catalyst was truly heterogeneous in nature.
Encouraged by the efficiency of the reaction protocol
described above, the scope of the Suzuki–cross coupling
reaction was studied with Fe3O4@CF-Pd(0) (0.5 mol % of
[Pd]) and K2CO3 as base using water as a reaction medium
We are thankful to the Director, IIP for his permission to
publish these results. MB is thankful to CSIR, New Delhi for
providing technical HR under the XII five year projects.
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o
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chicken feather (Fe3O4@CF-Pd(0))
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for 1h under sonication. The sonicated mixture was stirred at

5
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