Cellulose supported Pd(II) complex catalyzed carbon-carbon bonds formation

Article abstract of DOI:10.1166/jnn.2019.16289

Corn-cobs are an agro-industrial waste and composed of cellulose mostly. In this study cellulose was isolated from the waste corn-cobs and modified to polymeric hydroxamic acid palladium complex 1 and characterized by using a variety of spectroscopic methods such as field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The complex 1 exhibited high catalytic activity towards Suzuki and Heck coupling reactions of activated and deactivated aryl halides to give the respective coupling products with high yield. Moreover, the complex 1 was recovered and recycled five times with no considerable loss of catalytic overall performance.

Full text of DOI:10.1166/jnn.2019.16289

Article
Journal of
Nanoscience and Nanotechnology
Vol. 19, 2856–2861, 2019
Copyright © 2019 American Scientific Publishers
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Printed in the United States of America
Cellulose Supported Pd(II) Complex Catalyzed
Carbon–Carbon Bonds Formation
Shaheen M. Sarkar1ꢀ2ꢀ∗, S. S. Rashid2, Kaykobad Md. Rezaul Karim3ꢀ4, Siti Noor Hidayah Mustapha2,
Yuen Mei Lian2, Normaiza Zamri2, Md. Maksudur Rahman Khan3,
Emmet J. O’Reilly1, and Md. Lutfor Rahman5ꢀ∗
1Bernal Institute, Department of Chemical Sciences, University of Limerick, Castletroy, Limerick V94, Ireland
2Faculty of Industrial Sciences and Technology, Universiti Malaysia Pahang, Gambang 26300, Kuantan, Malaysia
3Faculty of Chemical and Natural Resources Engineering, Universiti Malaysia Pahang, Gambang 26300, Kuantan, Malaysia
4Chemistry Discipline, Khulna University, Khulna 9208, Bangladesh
5Faculty of Science and Natural Resources, Universiti Malaysia Sabah, Kota Kinabalu 88400, Sabah, Malaysia
Corn-cobs are an agro-industrial waste and composed of cellulose mostly. In this study cellu-
lose was isolated from the waste corn-cobs and modified to polymeric hydroxamic acid palladium
complex 1 and characterized by using a variety of spectroscopic methods such as field emission
scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDX), transmis-
sion electron microscopy (TEM), X-ray powder diffraction (XRD), X-ray photoelectron spectroscopy
(XPS) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The complex 1
IP: 95.85.68.20 On: Mon, 10 Dec 2018 02:07:26
exhibited high catalytic activity towards Suzuki and Heck coupling reactions of activated and deacti-
Copyright: American Scientific Publishers
vated aryl halides to give the respective coupling products with high yield. Moreover, the complex 1
Delivered by Ingenta
was recovered and recycled five times with no considerable loss of catalytic overall performance.
Keywords: Cellulose, Polymeric Hydroxamic Acid, Suzuki and Heck Reactions Palladium
Complex.
1. INTRODUCTION
to continuous demands of environmental friendly and
sustainable resources, efforts have been made to use
biopolymers in the exploration of solid support for metal
catalysts and processes. Recently, researches have been
applied several biopolymers,24ꢀ25 gelatin,26 starch,27 chi-
tosan derivatives28 and arabinogalactan29 as a support for
Pd-catalyzed reactions. The poor stability of biopolymer
supported metal catalysts and metal leaching properties
are considered as the major weaknesses in conjunction of
selectivity and recycling of the supported catalysts. Thus,
it is highly expected to prosper a common, simple bio-
heterogeneous metal catalysts, which can be applied to
a variety of substrates in metal catalyzed cross-coupling
reactions under mild conditions.
The biodegradable natural cellulose surface could be
modified and effective functional chelating groups would
be introduced.30–32 Only a few reports are available where
cellulose has been used as a solid support such as Pd-
catalyzed allylic alkylation,33 hydrogenations,34 and con-
densation reaction.35 However, the modifications of the
natural cellulose and its applications to the C–C bonds
Palladium catalyzed Suzuki-Miyaura and Mizoroki-Heck
cross-coupling reactions1ꢀ2 have acquired significant inter-
est as a synthetic tool for the development of C–C bond
that can be used for synthesis of bioactive molecules,3
natural products,4ꢀ5 drugs,6ꢀ7 agrochemicals8 and advanced
materials.9 In general, homogeneous Pd-complexes are
often used as an active catalyst for these coupling
reactions which required phosphine ligands and suf-
fer from numerous disadvantages. Therefore use of the
solid supported heterogeneous metal catalysts becomes
an extremely interesting element of the different cat-
alytic reactions as it allows easy isolation of prod-
ucts with regeneration of the catalyst. Currently, a lot
of efforts are invested to propose efficient, environmen-
tal friendly and general heterogeneous metal catalysts
through supporting of metals onto alumina,10 silica,11–16
mesoporous materials,17ꢀ18 active carbon/graphene19 and
polymers,20–22 magnetic nanoparticles.23 However, due
∗Authors to whom correspondence should be addressed.
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1533-4880/2019/19/2856/006
doi:10.1166/jnn.2019.16289

Sarkar et al.
Cellulose Supported Pd(II) Complex Catalyzed Carbon–Carbon Bonds Formation
formation reactions are limited.36–38 As a continuation of
our current studies on palladium catalyzed chemical bonds
formation,12ꢀ14 we herein report cellulose modified poly-
meric hydroxamic acid Pd(II) complex 1 as a highly effec-
tive heterogeneous metal catalyst for Suzuki and Heck
coupling reactions of activated and deactivated aryl halides
under mild reaction conditions without use of any addi-
tives. It was also found that complex 1 showed high cat-
alytic activity as well as reutilization capability.
polymeric hydroxamic acid modified cellulose supported
complex 1 (Scheme 1). To determine the loading amount
of palladium in complex 1, ICP-AES analysis was carried
out and found that 0.35 mmol/g of palladium was con-
tained in the complex 1. The FE-SEM micrograph analysis
was carried out to observe the surface morphology of poly-
meric hydroxamic acid chelating ligand and complex 1.
The FE-SEM analysis of chelating ligand showed small
spherical shape grain like surface (Fig. 1(a)) whereas, FE-
SEM image of the complex 1 displayed compact and big-
ger spherical morphology (Fig. 1(b)). The FE-SEM study
of chelating ligand and complex 1 indicated that the lig-
ands were coordinated with palladium species and pro-
vided aggregated compact bigger spherical morphology.
EDX (Fig. 1(c)) image of 1 showed the presence of pal-
ladium species onto the complex 1. The TEM images
(Fig. 1(d)) of complex 1 showed well distribution of the
palladium complex onto the cellulose backbone. The X-ray
diffraction study (XRD) of cellulose shows (Fig. 2(a))
three combination peaks at 2ꢂ values of 16.3ꢀ, 18.5ꢀ, and
23.8ꢀ corresponding to the Braggs planes (101), (101ꢁ) and
(002) respectively. The peaks at 33.0ꢀ, 53.6ꢀ and 58.7ꢀ in
the complex 1 were identified for the Pd(II) (101), (112)
and (103) planes respectively.40 These new peaks were fur-
ther confirmed the presence of palladium species in the
cellulose supported polymeric ligand. To confirm the oxi-
dation state of palladium we also carried out XPS analysis
2. EXPERIMENTAL DETAILS
2.1. Preparation of Complex 1
An aqueous solution of (NH4ꢁ2PdCl4 (300 mg in 60 mL
H2O) was slowly added to a stirred suspension of poly-
meric ꢀhydroxamic acid chelating ligand (1.5 g in 25 mL)
at 25 C. The resulting mixture was continuing to stirrer
for 3 h at 25 ꢀC and the resulting light brown colour com-
plex 1 was filtered on a glass filter, washed with water,
ꢀ
MeOH, and dried at 60 C for 3 h. The ICP-AES analysis
of complex 1 revealed that 0.35 mmol/g of palladium was
immobilized by the polymeric chelating ligand.
2.2. General Procedure for Suzuki Reaction
A 15 mL screw cap vial was charged with aryl halide
(1 mmol), benzeneboronic acid (1.2 mmol), K2CO3
(2 mmol) and complex 1 (0.02 mol%) in EtOH:H2O
ꢀ
of complex 1. The narrow-scan XPS spectra of complex 1
(1:1 mL). The reaction mixture wIaPs: h9e5a.t8e5d.6a8t .9200 OCn:foMr on, 10 Dec 2018 02:07:26
Copyright: American Scientific Publishers
exhibited (Fig. 2(b)) doublet peaks are at 337.62 eV and
4–10 h. The progression of reaction was monitored by
Delivered by Ingenta
342.81 eV corresponds to 3d5/2 and 3d3/2 those were
TLC or GC analysis. After complete consumption of the
aryl halide it was cooled to room temperature. The reaction
mixture was diluted with water and extracted with ethyl
acetate (4×5 mL). The ethyl acetate layer was dried over
MgSO4 and evaporated under reduced pressure. The result-
ing crude product was purified on a column chromatogra-
phy by using hexane/ethyl acetate (10:1) as an eluent.
assigned for the binding energies of palladium.41 The XPS
spectrum of 1 revealed that the polymeric hydroxamic acid
ligands were coordinated with palladium species and the
oxidation state of palladium was Pd(II).
After characterization of complex 1, we focused on
the application of 1 in the Suzuki coupling reaction of
aryl halide. Efficiency of the complex 1 was first exam-
ined by chosen 4-iodotoluene and benzeneboronic acid
as a model reaction. The reaction conditionꢀwas main-
tained by employing 0.02 mol% of 1 at 90 C for 4 h.
When the initial reaction was carried out in aqueous N,N-
dimethylformamide (DMF) in presence of 2 mmol of
K2CO3 the reaction was smoothly forwarded to afford
the corresponding coupling product 2a with 89% yield
(Table I, entry 1). However, the yield of 2a was not sig-
nificantly improved upon changing the solvent systems
(entries 2–4). Interestingly, the yield was improved to
95% when aqueous ethanol was used as a reaction media
(entry 5). However, the yield was dropped when K2CO3
was replaced by the other bases (entries 6–9). As it can be
seen in Table I, when the reaction was conducted out using
5 mol% of TBAB in water provided only 74% yield of 2a
(entry 10). In fact, the reaction can also be forwarded in
pure water with lower yield of 2a (entry 11).
2.3. General Procedure for Heck Reaction
A mixture of aryl halide (1 mmol), olefin (2 mmol), Et3N
(3 mmol), complex 1 (0.05 mol%) and 2 mL DMF were
placed in a 15 mL screw cap vial. The reaction mixture
was heated at 130 ꢀC for 7–12 h and the reaction progress
was continuously monitored by TLC/GC analysis. After
completion of the reaction, it was cooled at room temper-
ature. The coupling product was washed with water and
extracted with ethyl acetate. The ethyl acetate layer was
dried over MgSO4 and evaporated under reduced pressure.
The crude product was purified by column chromatogra-
phy by using hexane/ethyl acetate (1:5) as an eluent.
3. RESULTS AND DISCUSSION
The polymeric hydroxamic acid ligand was synthesized
and characterized followed by our previous report.39 The
ligand was mixed with aqueous ammonium tetrachloropal-
The reaction conditions of the Suzuki reaction was
optimized (Table I, entry 2) and then the applicability
ꢀ
ladate [(NH4ꢁ2PdCl4] at 25 C to afford the brown color
J. Nanosci. Nanotechnol. 19, 2856–2861, 2019
2857

Cellulose Supported Pd(II) Complex Catalyzed Carbon–Carbon Bonds Formation
Sarkar et al.
NHOH
C O
H
C
H
C
Cell
O
CH2
CH2CHCHCH2
C O
Cell
CH2
O
n
n
C O
O C
NHOH
NHOH
NHOH
Poly(hydroxamic acid)
(NH4)2PdCI4
r.t., 3 h
H
Cell
O
H2C
C
n
NH
O
O
Pd
O
O
HN
C
H
CH2
O
Cell
n
Pd(II) complex 1
IP: 95.85.68.20 On: Mon, 10 Dec 2018 02:07:26
Copyright: American Scientific Publishers
Delivered by Ingenta
Scheme 1. Preparation of complex 1.
of complex 1 was expanded by using different types of
aryl halides and organoboronic acids (Table II). The com-
plex 1 was efficiently forwarded the reaction of either
electron rich or deficient aryl iodides with benzeneboronic
acid to provide the corresponding biaryl products 2b–f
in 88–96% yields (entries 1–5). The complex 1 was
separated from the heterogeneous reaction mixture by
simple filtration and recurrently used five times without
considerable loss of its catalytic performance (entry 3).
Phenyl iodide and 4-iodoaacetophenone were also effi-
ciently coupled with 4-methoxybenzeneboronic acid to
give the desired products 2c with 90% and 2g with 89%
yield respectively (entries 6 and 7). The electron donat-
ing and electron withdrawing aryl bromides were smoothly
forwarded the reactions with 4-methoxybenzeneboronic
acid and 2-napthylboronic acid to afford the respective
biaryl products 2h–l in up to 91% yield (entries 8–12)
within 4–6 h. It should be noted that the less reactive aryl
chlorides were also smoothly coupled with benzeneboronic
acid and 2-napthylboronic acid to give the coupling prod-
ucts 2c–e, 2f and 2l with 83–90% yield (entries 13–17).
In order to check the efficacy of 1, a comparison studies
of Suzuki reactions were investigated in terms of reaction
temperature, time, and catalyst doses.42ꢀ43 Interestingly, we
observed that our catalytic system reveals higher perfor-
mance as compared to their reports.
After observing the high catalytic performance of the
complex 1 in the Suzuki coupling reaction, the cellulose
supported complex 1 was then further applied to the Heck
reaction with aryl iodide. To check the efficiency of com-
plex 1, initially the coupling between phenyl iodide and
butyl acrylate were chosen as a standard reactants. The
cross-coupling of phenyl iodide with butyl acrylate using
3 mmol of N,N-diisopropylethylamine (DIPEA) in DMA
with 0.05 mol% of 1 afforded the corresponding product
3a (73% yield) within 7 h at 130 ꢀC (Table III, entry 1). It
was observed that, when the same reaction was conducted
in DMSO (entry 2) only 72% yield was achieved. No
significant yields were observed upon the use of sodium
methoxide as a base (entries 3 and 4). However, when the
reactions were carried out in DMF by using of an organic
base i.e., DIPEA and Et3N smoothly forwarded the cou-
pling reaction to give 3a with 84% and 96% yields respec-
tively (entry 5 and 6). The organic base Et3N showed
better result (entry 6) compare to DIPEA. However the
yield was significantly dropped when the reaction was con-
ducted in presence of sodium methoxide (entry 7). Inter-
estingly, solvents were significantly enhance the reaction
to have an improved yield of the coupling product (entries
9 and 10). Hence, we assumed that 0.05 mol% of the
complex 1, Et3N (3 mmol) and DMF supposed to be an
ideal mixture for this Heck reaction (entry 6). However,
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Sarkar et al.
Cellulose Supported Pd(II) Complex Catalyzed Carbon–Carbon Bonds Formation
(a)
(a)
(b)
(b)
Pd3d5/2 337.62 (eV)
Pd3d3/2 342.81 (eV)
(c)
346
344
342
340
338
336
334
IP: 95.85.68.20 On: Mon, 10 Dec 2018 02:07:26 Energy (eV)
Copyright: American Scientific Publishers
Figure 2.
Delivered by Ingenta(a) XRD spectrum of cellulose and 1, (b) narrow-scan XPS
spectrum of 1.
Once the reaction conditions for the Heck coupling
reaction was optimized, the utility of the complex 1
was then expanded by using of a various types of aryl
halides and olefins (Table IV). Reaction between activated
and deactivated aryl iodides with a diversity of olefins
afforded the desired respective cross-coupling products
(d)
Table I. Screening of Suzuki reaction.ꢃaꢄ
1 (0.02 mol%)
+
I
B(OH)2
Me
Me
solvent (1:1)
90 ºC, 4h
2a
Entry
Base
Solvent
Yield (%)ꢃbꢄ
1
2
3
4
5
6
7
8
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K3PO4
NaOAc
NaOH
KOH
DMF:H2O
DMSO:H2O
NMP:H2O
THF
EtOH:H2O
EtOH:H2O
EtOH:H2O
EtOH:H2O
EtOH:H2O
H2O+TBAB
H2O
89
90
88
83
95
89
87
85
84
74
63
Figure 1. (a) FESEM image of polymeric hydroxamic acid, (b) FESEM
image of complex 1, (c) EDX image of 1, (d) TEM image of 1.
9
10
11
K2CO3
K2CO3
the complex 1 loading will be further decreased to
0.004 mol% which still effectively accelerated (entry 11)
the Heck reaction that provided high turnover frequency
(TON = 23,000).
Notes: ꢃaꢄConditions: Phenyl iodide (1 mmol), benzeneboronic acid (1.2 mmol),
base (2 mmol), and complex 1 (0.02 mol%) at 90 ꢀC for 4 h in 2 mL solvents.
ꢃbꢄYield after column chromatography.
J. Nanosci. Nanotechnol. 19, 2856–2861, 2019
2859

Cellulose Supported Pd(II) Complex Catalyzed Carbon–Carbon Bonds Formation
Table II. Scope of Suzuki reaction.ꢃaꢄ Table IV. Scope of Heck reaction.ꢃaꢄ
Sarkar et al.
R1
1 (0.02 mol%)
+
R2
B(OH)2
1 (0.05 mol%)
X
R1
R2
+
R1
K2CO3
EtOH:H2O(1:1)
90 ºC
I
Olefin
2
Et3N (3 mol equiv)
DMF,130 ºC
R
R
3
Yield (%)ꢃbꢄ
Entry
X
R1
R2
Time (h) Product Yield (%)ꢃbꢄ
Entry
X
R
Olefin
Product
1
2
3
4
5
6
7
8
I
I
I
I
I
I
I
Br
Br
Br
Br
Br
Cl
3-Me
4-MeO
4-NO2
4-CN
4-MeCO
H
4-MeCO 4-OMe
4-OMe
4-Me
Ph
Ph
Ph
Ph
Ph
4
4
4
4
4
4
4
6
6
6
6
4
8
8
8
10
8
2b
2c
2d
2e
2f
2c
2g
2h
2i
2j
2k
2l
2d
2f
2e
2c
2l
90
88
1
2
3
4
5
6
7
8
I
I
I
I
I
I
I
I
I
Br
Br
Br
Br
Br
Br
Br
Cl
Cl
Cl
Cl
Cl
Ph
4-Me
4-OMe
4-NO2
MA
BA
BA
BA
3b
3c
3d
3e
3f
3g
3h
3i
92
90
87
96, 85ꢃcꢄ
95
88
85
89
86
90
86
92
87
83
88
82
88
96, 88ꢃcꢄ
92
94
90
89
87
88
89
90
91
90
87
85
83
4-MeCO
4-Me
4-OMe
4-CN
4-OMe
Ph
4-OMe
4-NO2
Ph
4-Me
4-Me
4-OMe
Ph
4-Me
4-NO2
4-MeCO
Ph
BA
AA
AA
Sty
Sty
MA
MA
BA
AA
AA
Sty
Sty
BA
BA
BA
BA
Sty
4-OMe
4-OMe
4-OMe
2-nap
2-nap
2-nap
Ph
Ph
Ph
Ph
2-nap
9
9
3j
10
11
12
13
14
15
16
17
4-Me
10
11
12
13
14
15
16
17ꢃdꢄ
18ꢃdꢄ
19ꢃdꢄ
20ꢃdꢄ
21ꢃdꢄ
3b
3k
3e
3l
3g
3m
3j
3a
3c
3e
3f
4-CN
4-NO2
4-NO2
Cl 4-MeCO
Cl
Cl
Cl
4-CN
4-MeO
4-NO2
88
86
91
90
82
Notes: ꢃaꢄConditions: Aryl halide (1 mmol), benzeneboronic acid (1.2 mmol),
K2CO3 (2 mmol) and complex 1 (0.02 mol%) in 2 mL aqueous ethanol. ꢃbꢄIsolated
yield. ꢃcꢄFive reused of the complex 1.
3o
Notes: ꢃaꢄConditions: Aryl halide (1 mmol), olefin (2 mol equiv), complex 1
(0.05 mol%), Et3N (3 mol equiv), in DMF (2 mL) at 130 ꢀC for 7 h. ꢃbꢄYield
after column chromatography. ꢃcꢄFive reused of the complex 1. ꢃdꢄReaction time was
3b–3j with 85–96% yields (entries 1–9). It should be noted
that, the complex 1 was recovered from the heteroge-
neous reaction mixture and successively used five times
12 h. MA = Methyl acrylate, BA = Butyl acrylate, AA = N-isopropylacrylamide,
IP: 95.85.68.20 On: Mon, 10 Dec 2018 02:07:26
Sty = Styrene.
Copyright: American Scientific Publishers
with minor fall of its catalytic performance (entry 4). It
Delivered by Ingenta
was observed that the electron-donating aryl iodides pro-
vided lower yield in compare with the aryl iodides those
having electron withdrawing functional groups. The cou-
pling reaction was promoted efficiently in the presence of
N-isopropylacrylamide (AA) to give 3g and 3h with 88%
and 85% yields respectively (entries 6 and 7). Interestingly,
the corresponding product 3i and 3j with higher yield
(entries 8 and 9) were afforded smoothly when aryl iodides
coupled with less reactive and bulky styrene. Moreover,
this catalytic system was worked well to the less reac-
tive aryl bromides. The electron donating and withdraw-
ing aryl bromides were readily reacted with a variety of
alkenes to provide the corresponding Heck reaction prod-
ucts with 82–92% yields (entries 10–16). Interestingly, the
least reactive aryl chlorides were also underwent Heck
reaction to afford the corresponding coupling products
with high yield (entries 17–21). A comparison study was
investigated to evaluate the efficacy of 1 towards Heck
reaction. From the previous study it was found that13 com-
plex 1 exhibited better catalytic performance in terms of
catalyst loading.
Table III. Screening of Heck reaction.ꢃaꢄ
CO2Bu
1 (0.05 mol%)
I
+
CO2Bu
base, solvent
130 ºC,7h
3a
Entry
Solvent
Base
Yield (%)ꢃbꢄ
1
2
3
4
5
6
7
8
DMA
DMSO
DMA
DMSO
DMF
DMF
DMF
DMA
DMSO
NMP
DIPEA
DIPEA
NaOMe
NaOMe
DIPEA
Et3N
NaOMe
Et3N
Et3N
73
72
70
68
84
96
75
93
79
88
92
4. CONCLUSION
In conclusion, corn-cob cellulose modified complex 1 was
prepared and characterized. The supported palladium com-
plex 1 was successfully applied to the Suzuki coupling
reaction of aryl halides with a various organoboronic acids
to afford the corresponding biaryl produces in up to 96%
yield. It was also found that the complex 1 promoted Heck
reaction efficiently a varieties of aryl halides with olefins
to give the desired coupling products with excellent yield.
9
10
11ꢃcꢄ
Et3N
Et3N
DMF
Notes: ꢃaꢄConditions: Phenyl iodide (1 mmol), butyl acrylate (2 mmol), complex 1
(0.05 mol%) and base (3 mmol) in the solvent (2 ml) for 7 h. ꢃbꢄDodecane was used
as an internal standard to calculate GC yields. ꢃcꢄReaction was performed using
phenyl iodide (12 mmol scale) for 10 h.
2860
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Sarkar et al.
Cellulose Supported Pd(II) Complex Catalyzed Carbon–Carbon Bonds Formation
Additionally, the complex showed remarkable reusability
without considerable loss of catalytic activity.
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Acknowledgments: The authors would like to express
heartfelt thanks to the Ministry of Education Malaysia,
FRGS grant no. RDU 140124.
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Received: 21 May 2018. Accepted: 1 August 2018.
J. Nanosci. Nanotechnol. 19, 2856–2861, 2019
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