An efficient parts-per-million α-Fe2O3 nanocluster/graphene oxide catalyst for Suzuki-Miyaura coupling reactions and 4-nitrophenol reduction in aqueous solution

Article abstract of DOI:10.1039/c6cc08401j

A new α-Fe₂O₃ nanocluster/graphene oxide catalyst is found to be efficient in parts-per-million for Suzuki-Miyaura coupling and 4-nitrophenol reduction in aqueous solution, and this catalyst is recycled at least 4 times in good yields.

Full text of DOI:10.1039/c6cc08401j

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αꢀFe2O3 nanocluster supported onto graphene oxide catalyst is shown for the first time to catalyze
Suzuki–Miyaura coupling and 4ꢀnitrophenol reduction in aqueous solution with only
partsꢀperꢀmillion loading.

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Efficient partsꢀperꢀmillion αꢀFe2O3 nanocluster/graphene oxide
catalyst for Suzuki–Miyaura coupling reactions and
4ꢀnitrophenol reduction in aqueous solution
Received 00th January 20xx,
Accepted 00th January 20xx
Changlong Wang,a,b Lionel Salmon,b Roberto Ciganda,a,c Luis Yates,d Sergio Moya,d Jaime Ruiz,a
DOI: 10.1039/x0xx00000x
and Didier Astruca*
www.rsc.org/
A new αꢀFe2O3 nanocluster/graphene oxide catalyst is found to through supramolecular Hꢀbonding interactions
be efficient in partsꢀperꢀmillion for Suzuki–Miyaura coupling between the PEG termini of the tristrzꢀPEG ligand and
and 4ꢀnitrophenol reduction in aqueous solution, and this the functional groups of the GO support, followed by
catalyst is recycled at least 4 times in good yields.
filtration and drying (Scheme S1, and SI). The Fe
content was checked by inductively coupled plasma
atomic emission spectroscopy (ICPꢀAES) analysis
indicating that > 99% of the αꢀFe2O3 nanocluster was
deposited onto GO.
Metalꢀcatalyzed crossꢀcoupling carbon–carbon (CꢀC)
bond formation has significantly advanced organic
synthesis.1 In particular, Pdꢀcatalyzed Suzuki–Miyaura
(SM) coupling has been efficiently used in numerous
procedures for the constructions of CꢀC bonds.2
Although chemists have successfully decreased the
amounts of precious Pd catalyst in such reactions,3
alternative methodologies to accomplish a similar
catalytic SM coupling using “Green Chemistry”, and
especially cheap biometal catalysts (for instance Fe,4
Ni,5 or Cu,6) are highly encouraged. Nevertheless
wellꢀdefined alternative approaches most often result
in the requirements of specific ligands, high catalyst
loading, or hash reaction conditions and sometimes
suffer from poor catalytic efficiency. Herein, we
report a new heterogeneous catalytic system, αꢀFe2O3
nanocluster/graphene oxide (αꢀFe2O3/GO),
1, for
efficient SM coupling reactions in aqueous solution
and reduction of 4ꢀnitrophenol (4ꢀNP) in water
employing only ppm amounts of catalyst.
Figure 1. (a) and (b) TEM images of the αꢀFe2O3 nanoꢀ
cluster/GO catalyst; (c) Corresponding EXD analysis of the
The synthesis of the novel heterogeneous catalyst
1 is
area in (b). (d) HRTEM of αꢀFe2O3 nanocluster/GO catalyst 1.
carried out in water. It first involves addition of an
aqueous solution of FeCl3 to the preꢀsolubilized
amphiphilic tris(triazolyl)ꢀpolyethylene glycol (trisꢀ
trzꢀPEG)7 ligand in water followed by reduction using
NaOH. This preꢀcatalyst is then deposited on GO
The TEM images showed that αꢀFe2O3 nanoclusters of
only 1.8 nm size were homogeneously deposited on
the edge of the GO sheets (Figure 1a, b). EDX
analysis then showed the Fe, C, N, and O signals
provided by the αꢀFe2O3 nanocluster/GO sample
(Figure 1c). The phase structure of this catalyst
1 was
further characterized by HRTEM analysis showing the
wellꢀdefined hexagonal shape and the lattice fringe
pacing of 0.25 nm corresponding to the (110)
crystallographic plane of the αꢀFe2O3 crystal (Figure
1d). The oxidation state of the Fe constituent in
1 was
checked by Xꢀray photoelectron spectroscopy (XPS).
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The XPS survey spectrum (Fig. S2) indicates that the
sample contains C, O and Fe. In the C 1s spectrum, the
peaks at 284.4, 286.4, 288.3 and 290.8 eV are
attributed to CꢀC, CꢀO, C=O, and OꢀC=O
configurations, respectively.8 The core level binding
energies located at 726.4 and 712.3 eV are shown in
Encouraged by the remarkable efficiency of 1 obtained in
the 4ꢀNP reaction, the catalytic performances have been
further investigated in the Suzuki–Miyaura coupling
reaction between bromobenzene and phenylboronic acid.
This reaction was conducted at 80℃ under a nitrogen
the Fe 2p spectrum, which correspond to Fe 2p1/2 and atmosphere for 24 h in the presence of 150 ppm mol%
Fe 2p3/2 core level of the αꢀFe2O3, respectively.9 catalyst and K2CO3 as the base. Optimizations of the SM
Moreover, the shakeup satellite peak at about 719.0
eV,10 a characteristic for the Fe3+ species, is also
clearly seen.
coupling reaction were first conducted by leaving the
solvent as the only parameter. Solvent mixtures containing
water and, as coꢀsolvent, DMF, ethylene glycol or EtOH
were tested for this model reaction. The results showed
that the presence of the H2O/EtOH solution led to the best
catalytic performance with a quantitative conversion and a
87% isolated yield. The amount of solvent is crucial in this
SM reaction, as a larger amount of the H2O/EtOH solvent
leads to lack of conversion, while low amounts of solvent
allow the reaction to proceed well (SI). These results
indicate that the concentration of the substrates is crucial
for this reaction.1d
Catalytic applications of the new catalyst 1 were first
probed for the 4ꢀNP reduction by NaBH4 in water,11
a
trusted test reaction pioneered by Pal’s group11a to explore
the catalytic efficiency of nanoparticles surfaces. Indeed
this reaction hardly proceeds in the absence of metal
catalyst.11 In the presence of the catalyst 1 in an aqueous
solution containing 4ꢀNP (1 equiv.) and NaBH4 (81
equiv.), reduction proceeds with an induction time (t0) of
1160 s (Figure 2). This feature suggests required activation
and dynamic restructuring of the αꢀFe2O3 nanocluster
surface, as shown by Ballauff’s group with AuNP and
PdNP catalysts.11d,g,h Following the induction time, 4ꢀNP
reduction proceeds very well, with an apparent kinetic rate
constant (kapp) of 4.17×10ꢀ4 s-1 (Figures S3 up). Given the
addition of such a low amount of the catalyst 1 (150 ppm
per 4ꢀNP), its catalytic efficiency is remarkable and even
superior to the best nobel metal nanoparticles catalysts.
Control experiment conducted in the presence of GO alone
indicated that the reaction did not proceed at all.
XPS was used to characterize the Fe oxidation state after
the SM reaction, but no Fe (0) was found, indicating that
EtOH does not reduce αꢀFe2O3 under the present
conditions (Figure 12).
In order to identify the actual active phase, ICPꢀAES
analysis was conducted to exclude the possibility of traces
Pd residues in 1, because ppm levels of Pd are known to be
sufficient for the catalysis of SM reactions. ICPꢀAES
analysis showed that there was no residual Pd (or below
the detection limit of 0.5 ppm) in 1. Control experiments
have also been conducted using either GO or αꢀFe2O3 as
the tentative catalyst for this model SM reaction, and no
reaction occurred under these conditions. To investigate
the homoꢀ or heterogeneity of the αꢀFe2O3 nanocluster/GO
system, a hot filtration test was conducted. The standard
SM reaction between bromobenzene and phenylboronic
acid proceeds well in the presence of the catalyst, whereas
removal of the catalyst at half way inhibited continuation
of the reaction (Figure 13). Thus the SM reaction by αꢀ
Fe2O3/GO occurs heterogeneously. It was also conducted
in the presence of αꢀFe2O3/active carbon for comparison,
and this reaction occurred with poor yield (23%). Thus it is
concluded that 1 catalyzes the SM reaction, and the
presence of the GO enhances the catalyst efficiency. The
high surface area of the GO support increases the
concentration of substrates near the αꢀFe2O3 catalyst and
its efficiency.13
Highꢀresolution UVꢀvis. was used to monitor the
reaction process by mixing αꢀFe2O3/GO and NaBH4
(
Figures S3 bottom). The spectra did not change during
the reaction, and no peaks at 352ꢁnm and at 262ꢁnm
that corresponded to Fe(0) were observed, suggesting
that the Fe(0) is not involved in the reaction. To
address the ironꢀleaching problem, we have conducted
4ꢀNP reduction after the removal of αꢀFe2O3/GO
catalyst by simple filtration. The yellow color of the
reaction mixture did not change during 2 days, and the
hotꢀfiltration test was negative (vide infra), suggesting
that leaching of soluble Fe(0) species does not account
for the reaction mechanism. It cannot be excluded that
tiny amounts of Fe(0) be formed, however, and serve
as catalyst.12
Given the optimized reaction conditions and high
efficiency of the catalyst 1, the scope of the SM coupling
reaction was examined with 1 (150 ppm) in the mixture of
EtOH and H2O under nitrogen atmosphere at 80℃ within
24 h (Table 1). A series of bromobenzene derivatives
bearing various substituents were tested for the SM
coupling reactions with phenylboronic acid under the
optimized condition.
Figure 2. (a) UVꢀvis. spectra for the 4ꢀNP reduction by NaBH4
catalyzed by 1; (b) consumption rate of 4ꢀNP: ꢀln(Ct/C0) vs. time.
2 | J. Name., 2012, 00, 1-3
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Moreover, recycling of the catalyst was also shown to be
Table 1. Investigation of the substrate scope in the Suzukiꢀ excellent. The mechanism of catalytic activation by αꢀ
Miyaura reaction catalyzed by αꢀFe2O3 nanocluster/GO.a
Fe2O3/GO remains unclear in these two reactions,
especially since no Fe(0) was detected. Also note that the
lack of extension of the SuzukiꢀMiyaura reaction to alkyl
bromides and alkylboronic acids is a limitation that will
need be taken into account in mechanistic investigation of
such catalytic systems.
Overall, the principles and results presented herein should
significantly contribute developing the ‘‘Green Chemistry”
applications involving earthꢀabundant metal heterogeneous
catalysts.
Entry
R1
H
R2
H
H
H
H
H
H
H
Conversionb
100%
100%
100%
100%
95%
98%
90%
75%
98%
Yieldc
87%
83.3%
83%
84.5%
80%
78%
75%
51%
82%
1
2
3
4
5
6
7
8
9
4ꢀNO2
4ꢀCHO
4ꢀCH3CO
4ꢀNH2
4ꢀCH3O
4ꢀCH3
H
Financial support from the China Scholarship Council
(CSC) of the People’s Republic of China (grant to C.W.),
the Universities of Bordeaux, Toulouse 3, the LCC
(Toulouse), and the Centre National de la Recherche
Scientifique (CNRS) is gratefully acknowledged.
2ꢀCH3
4ꢀCH3
H
a Reaction condition: bromobenzene (0.2 mmol), phenylboronic acid
(0.3 mmol), catalyst (150 ppm αꢀFe2O3), K2CO3 (0.4 mmol),
EtOH/H2O (1 mL/1 mL), 80℃, N2, 24 h; 1H NMR conversion;
b
c
Notes and references
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derivatives
containing
electronꢀ
withdrawing (NO2, CHO, CH3CO) and electronꢀdonating
(NH2, CHO, CH3) groups in para position were suitable
coupling partners, and the corresponding coupling
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bromopentane and nꢀbutylboronic acid, however.
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reaction was successfully recycled four times (SI), and
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