Reduction of aromatic compounds with Al powder using noble metal catalysts in water under mild reaction conditions

Article abstract of DOI:10.1016/j.crci.2013.09.013

In water, Al powder becomes a powerful reducing agent, transforming in cyclohexyl either one or both benzene rings of aromatic compounds such as biphenyl, fluorene and 9,10-dihydroanthracene under mild reaction conditions in the presence of noble metal catalysts, such as Pd/C, Rh/C, Pt/C, or Ru/C. The reaction is carried out in a sealed tube, without the use of any organic solvent, at low temperature. Partial aromatic ring reduction was observed when using Pd/C, the reaction conditions being 24 h and 60 °C. The complete reduction process of both aromatic rings required 12 h and 80 °C with Al powder in the presence of Pt/C.

Full text of DOI:10.1016/j.crci.2013.09.013

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´
Full paper/Memoire
Reduction of aromatic compounds with Al powder using noble
metal catalysts in water under mild reaction conditions
*
Ummey Rayhan, Hyeokmi Kwon, Takehiko Yamato
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan
A R T I C L E I N F O
A B S T R A C T
Article history:
In water, Al powder becomes a powerful reducing agent, transforming in cyclohexyl either
one or both benzene rings of aromatic compounds such as biphenyl, fluorene and 9,10-
dihydroanthracene under mild reaction conditions in the presence of noble metal
catalysts, such as Pd/C, Rh/C, Pt/C, or Ru/C. The reaction is carried out in a sealed tube,
without the use of any organic solvent, at low temperature. Partial aromatic ring reduction
was observed when using Pd/C, the reaction conditions being 24 h and 60 8C. The complete
reduction process of both aromatic rings required 12 h and 80 8C with Al powder in the
presence of Pt/C.
Received 18 August 2013
Accepted after revision 23 September 2013
Available online xxx
Keywords:
Reduction of aromatic compounds
Al powder
Noble metal catalysts
Water
ß 2013 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
Cyclohexane ring
1. Introduction
reaction should be conducted under anhydrous, strongly
reducing and basic conditions. These reaction conditions
The reduction of aromatic ring is a useful and important
technique for obtaining a variety of cyclohexane deriva-
tives. Because of the stabilization of the aromatic ring by
resonance hybridization, aromatic hydrocarbons are sel-
dom hydrogenated at room temperature over base metals
and palladium catalysts [1]. However, at elevated tem-
peratures and pressures, most aromatic hydrocarbons are
hydrogenated without difficulty over nickel and cobalt
catalysts [2–4]. Over ruthenium and particularly, over
rhodium and platinum, benzene and its derivatives are
hydrogenated at considerable rates, even at room tem-
perature [5–7]. Previously reported methods for develop-
ing cyclohexane rings from arenes are classified into two
types of reactions:
cannot be tolerated by some co-existing functional
groups, such as esters and ketones. Moreover, large
amounts of metal waste are produced from the reducing
agents in these reactions;
ꢀ
another one is hydrogenation with a transition metal
catalyst, which is a simple, convenient and sustainable
method [14,15]. Although some homogeneous catalysts
promote arene hydrogenation efficiently [16,17], the
presence of residual metal in the products makes the
industrial application of this method difficult. On the
other hand, the hydrogenation of arenes through the use
of heterogeneous metals (Ni, Rh, Ru, Pt and Pd) [15] has
some advantages, such as easy handling, lesser metal
contamination in the products and reusability, which
would make it suitable for industrial production.
ꢀ
one is the reduction with greater than stoichiometric
amounts of reducing agents, such as LiAlH4, borane
derivatives [8–11], or dissolving metals (Birch reduction)
[12,13]. These reagents are moisture-sensitive and the
Catalytic hydrogenation of organic compounds with
catalysts and hydrogen gas is one of the most useful
methods in the field of organic synthesis [18–20]. It was
reported by Tashiro’s group that aromatic compounds
were reduced to the corresponding cyclohexane products
in high yields, by using Raney Ni–Al [21]. Recently,
Maegawa et al. reported the convenient reduction of
*
Corresponding author.
E-mail address: yamatot@cc.saga-u.ac.jp (T. Yamato).
1631-0748/$ – see front matter ß 2013 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
http://dx.doi.org/10.1016/j.crci.2013.09.013
Please cite this article in press as: Rayhan U, et al. Reduction of aromatic compounds with Al powder using noble metal
catalysts in water under mild reaction conditions. C. R. Chimie (2014), http://dx.doi.org/10.1016/j.crci.2013.09.013

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aromatic compounds by a hydrogenation procedure based
on the use of heterogeneous platinum group catalysts. Rh/
C is the most effective catalyst for the hydrogenation of the
aromatic ring, which can be conducted in iPrOH under
neutral conditions and at ordinary to medium H2 pressures
(< 10 atm) [22]. They also reported the solvent-free and
solid-phase hydrogenation of various reducible function-
alities, which was effectively catalyzed by heterogeneous
palladium on carbon (Pd/C) [23]. Palladium catalysts
embedded on molecular sieves (MS3A and MS5A) were
also developed for chemoselective hydrogenation [24].
Wang et al. developed polymeric mesoporous carbon
graphitic nitrides (mpg-C3N4) and ordered mesoporous
graphitic carbon nitrides (ompg-C3N4), which were used to
prepare palladium catalysts (Pd@C3N4). These catalysts
demonstrated excellent activity and selectivity for hydro-
genation of quinoline to 1,2,3,4-tetrahydroquinoline under
mild temperatures (30–50 8C) and H2 pressure (1 bar) [25].
A green approach was reported about the hydrogenation of
bisphenol A (BPA) utilizing a special Ru catalyst in water
medium [26]. Utilization of water as a chemical reagent is
an essential aspect of green chemistry [27]. Water has
many advantages as a solvent for organic reactions from
the aspects of cost, safety, operation simplicity, and
environmental concerns as compared to the use of an
organic solvent [28–30].
In the above-mentioned literature, different aspects of
aromatic ring reduction were discussed. In present study,
we investigated the reduction of aromatic compounds
using Al powder with Pd/C, Rh/C, Pt/C and Ru/C in water
under atmospheric pressure at lower temperature. Biphe-
nyl, fluorene, and 9,10-dihydroanthracene were selected
because they were employed as model compounds in
pioneering works [21,22,31]. To the best of our knowledge,
there is no literature referring to any partial and complete
aromatic ring reduction technique utilizing Al powder
with these catalysts at lower temperature in water. In this
article, we developed new method for partial and complete
aromatic ring reduction using Al powder with commer-
cially available Pd/C and Pt/C, respectively.
Pd/C, Ru/C and Rh/C (20 mg) (4.5 mol% metal) was added
water (0.5 mL) (Wako distilled water). After heating at 60–
80 8C for 12–24 h, the mixture was cooled to room
temperature. The solution was diluted with 1 mL of water
and then stirred overnight at room temperature in a sealed
tube. After 24 h, the solution was extracted with diethyl
ether (2 mL Â 3) following the reported procedures [32].
The organic layer was combined, dried with MgSO4,
filtered through a cotton layer and concentrated in vacuum
to give the corresponding hydrogenated product. The
yields were determined by GLC analysis by using the
standard compound (1,2,3,4-tetrahydronaphthalene) and
the products were identified by GC–MS.
3. Results and discussion
In our present research work, we tried to reduce biphenyl
without using any alkaline solution, isopropyl alcohol or any
extra hydrogen pressure at lower temperature. To acquire
the optimized reaction conditions (i.e. catalysts, reaction
time and temperature), hydrogenation of biphenyl was
carried out using Al powder at 60 8C for 12 h in water in the
sealed tube; hydrogenationwas not initiated. Prolonging the
reaction time (24 h) and increasing the reaction temperature
at 120 8C (12 h) afforded the same results. Hydrogenation
proceededin thepresenceof aco-catalyst(Pd/C,Rh/C, Pt/Cor
Ru/C); and the results are shown in Table 1 (Scheme 1).
The benzene rings of biphenyl were reduced to afford a
mixture of cyclohexylbenzene (2a) and cyclohexylcyclo-
hexane (3a) in 10 and 84% yield, respectively, along with
the recovery of biphenyl (1a) in 6% yield at 60 8C using Pt/C.
Consequently, we have succeeded in reducing both
benzene rings of biphenyl (1a) to obtain cyclohexylcyclo-
hexane (3a) in quantitative yield by increasing the reaction
temperature to 80 8C (Table 1; entry 3). When Pd/C and Rh/
C were used as co-catalysts under the same reaction
conditions, the partial reduction of biphenyl (1a) afforded
cyclohexylbenzene in 54–60% yield (2a) along with the
recovery of the starting compound (1a) (Table 1; entries
4,5,7). In the case of Ru/C, only 35% of the compound 2a
was observed under the used reaction conditions. Thus, it
2. Experimental
Table 1
2.1. Materials and apparatus
Reduction of biphenyl (1a) by using Al powder in H2O in the presence of a
co-catalysta,b
.
All melting points are uncorrected. 1H NMR spectra
were recorded at 300 MHz on a Nippon Denshi JEOL FT-300
NMR spectrometer in CDCl3 with Me4Si as an internal
reference. IR spectra were measured as KBr pellets on a
Nippon Denshi JIR-AQ2OM spectrometer. Mass spectra
were obtained on a Shimadzu GC–MS-QP5050A Ultrahigh
Performance Mass Spectrometer AOC-20I, 100 V using a
direct-inlet system. GLC analyses were performed with a
Shimadzu gas chromatographer GC-2010.
Entry
Co-catalyst
Temp (oC)
Yield [%]d
2a
3a
Recovery 1a
1
None
Pt/C
60
60
80
60
80
80
80
60
60
0
10
0
0
100
6
2
84
100
0
3
Pt/C
0
4
Pd/C
Pd/C
Ru/C
Rh/C
Pd/C
Rh/C
54
59
35
60
91
7
46
19
26
29
4
5
22
39
11
5
6
7
8c
9c
90
3
2.2. General procedure for the reduction of aromatic
compounds
a
Substrate: 20 mg (0.13 mmol), co-catalyst: 4.5 mol% (metal), Al
powder: 100 mg (500 wt%), H2O: 0.5 mL.
b
Conditions: time, 12 h.
c
To the mixture of substrate (20 mg, 0.13 mmol) (Wako),
Conditions: time: 24 h.
d
Al powder (500 wt%) (53–150
m
m, 99.5%) (Wako) and Pt/C,
The yields were determined by GLC.
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catalysts in water under mild reaction conditions. C. R. Chimie (2014), http://dx.doi.org/10.1016/j.crci.2013.09.013

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3
Al powder/
co-catalyst
Al powder/
co-catalyst
CH2
in H2O
H2O, Δ
in the sealed tube
80 oC for 12 h
in the sealed tube
1b
1a
CH2
CH2
2b
3b
3a
2a
Scheme 2. Reduction of diphenylmethane (1b) by using Al powder in
Scheme 1. Reduction of biphenyl (1a) by using Al powder in H2O in the
H2O in the presence of a co-catalyst.
presence of a co-catalyst.
could be noted that the Pt/C catalyst has a higher activity
than Pd/C, Ru/C, and Rh/C (Table 1; entries 5–7).
In the presently developedmethod, wehave succeeded to
reduce the benzene rings of biphenyl and diphenylmethane
for the first time by using noble metal catalysts and Al
powder in water under mild reaction conditions without
using any organic solvent at lower temperature under
atmospheric pressure. Maegawa et al. also reported the
reduction of diphenylmethane and other aromatic com-
pounds by using Rh/C (10 wt%) catalyst under high
hydrogen pressure in isopropylalcohol as an organic
solvent [22].
For obtaining partial reduction of biphenyl using Pd/C
and Rh/C, the reaction time was increased to 24 h. In the
case of Pd/C, cyclohexylbenzene (2a) was obtained in 91%
yield at 60 8C, while Rh/C afforded cyclohexylcyclohexane
(3a) in quantitative yield under the same reaction
conditions (Table 1, entries 8, 9). For the different catalytic
activities of Pd/C and Rh/C, they showed different
selectivities to reduce the benzene ring of biphenyl (1a).
We investigated the reduction kinetics using Al powder
with the co-catalyst Pt/C, as it is the most powerful co-
catalyst; the results are summarized in Table 2. We
observed that the yield of the desired compound 3a was
increasing with time. On the other hand, the maximum
yield for 2a was found at 6 h (34%); after that, 2a was
gradually converted to 3a with time, and quantitative yield
was observed at 12 h.
We also investigated the hydrogenation of diphenyl-
methane (1b) with Al powder in the presence of noble
metal catalysts in water in the sealed tube under the same
reaction conditions as those used in the case of biphenyl
(1a). Both benzene rings of diphenylmethane (1b) were
reduced with Al powder in the presence of Pt/C to afford
bicyclohexylmethane (3b) in 88% yield along with the
recovery of 7% of diphenylmethane (1b). Unfortunately,
lower partial reduction products (2b) were observed when
using Pd/C (28%), Ru/C (25%) and Rh/C (41%) as co-
catalysts. This suggests that the lack of extended conjuga-
tion of diphenylmethane is responsible for the lower
partial reduction (Scheme 2).
After that, we performed the partial reduction of
various types of aromatic compounds with the Pd/C
catalyst under the same reaction conditions (Table 3). It
is noteworthy that biphenyl (1a) possesses a flexible
skeleton, but the partial reduction proceeds in a high yield.
In this case, benzene rings are not in the same plane. We
observed that diphenylmethane converted to lower
amounts of cyclohexylphenylmethane (2b) along with
large amount of recovery. Diphenylmethane slightly
comes up to Pd/C metal surface because the rapid rotation
of two phenyl groups centers methylene group. To ensure
this, we further examined diphenylethane (1c) under the
same reaction conditions. The similar result was also
obtained for one benzene ring reduction (2c, 45%) with
recovery (55%) of the starting compound. In addition,
fluorene (1d) and 9,10-dihydroanthracene (1e) afforded
high yields of partial reduction of one benzene ring owing
to their rigid structure. Sajiki et al. developed special Pd
catalysts and these catalysts achieved unique chemose-
lective hydrogenations of alkyne, alkene and azide
functionalities of benzene derivatives under hydrogen
atmosphere at room temperature [24]. In our case,
commercially available Pd/C with Al powder give the
partial reduction of aromatic compounds where water is
the proton source. Recently, Wang et al. developed new
catalysts using Pd and observed selectivity in the hydro-
genation of quinoline to 1,2,3,4-tetrahydroquinoline at
mild temperatures (30–50 8C) and under H2 pressure
(1 bar) [25]. But in our case, we did not apply extra
hydrogen pressure to reduce the benzene ring.
Table 2
Reduction of biphenyl (1a) by using Al powder in the presence of Pt/Ca,b
.
Entry
Time (h)
Yield [%]c
2a
3a
Recovery 1a
1
2
3
4
5
6
7
2
4
5
12
34
23
15
0
0
1
95
87
52
24
6
We further investigated fused aromatic compounds,
such as fluorene 1d, 9,10-dihydroanthracene 1e, anthra-
cene as well as diphenylether 1f and diphenylamine 1g.
The results are compiled in Table 4.
6
14
53
8
10
12
14
79
100
100
0
0
0
Fluorene (1d) was treated under similar reaction
conditions. From the figure (Supplementary data, ESI,
Fig. S31), we found that the Ru/C catalyst is the most
inactive for the hydrogenation of the benzene ring.
a
Substrate: 20 mg (0.13 mmol), co-catalyst: 4.5 mol% (metal), Al
powder: 100 mg (500 wt%), H2O: 0.5 mL.
b
Condition: temperature: 80 8C.
The yields were determined by GLC.
c
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Table 3
Reduction of aromatic compounds (1) by using Al powder in the presence of Pd/Ca,b
.
Entry
1
Substrate (1)
Product (2)
Yield [%]c,d
91 [70]
Recovery (1)
4
1a
2a
35 [25]
45 [30]
65
55
2
3
CH2
2b
CH2
1b
CH2
CH2
CH2 CH2
2c
1c
77 [52]
90 [70]
16
4
1d
2d
6
5
2e
1e
a
Substrate: 20 mg, co-catalyst: 4.5 mol% (metal), Al powder: 100 mg (500 wt%), H2O: 0.5 mL.
Conditions: temperature: 60 8C, time: 24 h.
The yields were determined by GLC.
b
c
d
Isolated yields are shown in square brackets.
Compared to biphenyl, both Rh/C and Pd/C are effective
applying extra hydrogen pressure through the formation
of 9,10-dihydroanthracene [35,36].
catalysts for fluorene reduction. The Pt/C catalyst has
almost the same reactivity as that of the biphenyl (1a). It
is also reported that fluorene (1d) is converted princi-
pally into hexahydrofluorene (3d) over Pd–Al2O3 (71%
yield) and into perhydrofluorene over Rh–Al2O3 (72%
yield) in decalin at 200 8C and 7 MPa H2 [33]. Pt–Al2O3
showed a much lower activity under the same condi-
tions. Treatment of fluorene (1d) with Raney Ni under
refluxing toluene in the presence of triethylamine leads
to the exclusive formation of cis-hexahydrofluorene [34].
After that, 9,10-dihydroanthracene and anthracene were
treated with the metal catalysts under the same
conditions as those described above. In the case of
9,10-dihydroanthracene, we obtained 97% yield of the
reduction product (3e) of both benzene rings. Unfortu-
nately, lower yields were obtained from anthracene in
these conditions. The yields of tetradecahydroanthra-
cene (3e), octahydroanthracene (2e), and 9,10-dihy-
droanthracene (1e) were 43.4%, 49.4%, and 1.2%,
respectively, with 6% recovery of anthracene. When
the reaction time was increased to 24 h at 80 8C,
tetradecahydroanthracene (3e) in 97% yield and octahy-
droanthracene (2e) in 3% yield were obtained. It is also
reported that anthracene is hydrogenated over copper–
chromium in ethanol at 100 8C or in decalin at 150 8C
Furthermore, we tried to reduce heteroatom-contain-
ing aromatic compounds diphenylether and diphenyla-
mine using Al powder with Pt/C. In our conditions,
diphenylether gave a small amount of benzene ring
reduction, but it produced cyclohexanol in higher yield.
Interestingly, in the case of diphenylamine, we achieved a
higher yield of dicyclohexylamine along with cyclohex-
ylamine and cychohexanol under mild reaction conditions,
as previously reported [37].
Finally, we examined the substituent effect of biphenyl
to obtain the complete reduction product by using Al
powder with Pt/C under the same reaction conditions. We
obtained high yields (83%) of the reduction product of the
benzene ring with cis and trans products for 4-methylbi-
phenyl. In the case of 4-methoxy- and 4-tert-butylbiphe-
nyl, the yield of 3 decreased to 20 and 45% yield. In fact, for
4-methoxybiphenyl, we have also observed the formation
of compounds 1a, 2a and 3a under the conditions used.
These results strongly suggest that the presently devel-
oped reducing agent not only reduces the benzene ring, but
also cleaves the polar C–O bond. In the case of 4-tert-
butylbiphenyl comparatively higher yields (48%) of 4-tert-
butylcyclohexylbenzene were obtained. Because of the
steric effect of the tert-butyl group, the benzene ring
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5
Table 4
Reduction of aromatic compounds (1) by using Al powder in the presence of Pt/Ca,b
.
Entry
1
Substrate
Product yield [%]c,d
Recovery (1a)
1a
2a (0)
3a (100) [90]
0
7
C
C
C
2
3
4
H2
H2
H2
1b
3b (88) [69]
3d (81) [72]
3e (97) [77]
2b (5)
11
0
1d
2d (8)
1e
2e (3)
13
OH
O
O
5
1f
3f (20) [17]
4 (67)
NH2
4 (17)
5 (3)
6
NH
1g
NH
6
3g (74) [60]
a
Substrate: 20 mg, co-catalyst: 4.5 mol% (metal), Al powder: 100 mg (500 wt%), H2O: 0.5 mL.
Conditions: temperature: 80 8C, time: 12 h.
The yields were determined by GLC.
b
c
d
Isolated yields are shown in square brackets.
Al powder/ Pt/C
directly attached to it cannot be easily reduced on the
catalyst’s surface. We also observed only one compound,
which is 4-tert-butylcyclohexylbenzene, by spectroscopic
analysis. We can assume that another benzene ring,
which bears no tert-butyl group, can be easily reduced;
chemoselectivity was observed. Moreover, as tert-butyl
group is a bulky group, the tert-butyl substituent cannot
approach parallel to the metal surface to give high yields of
the reduction product of both benzene rings. From these
results, we can conclude that the approach of the
substituted biphenyl towards the highly porous surface
of the Pt metal catalyst depends on the substituent
(Scheme 3 and Table 5).
R
in H2O
80 oC for 12 h
in the sealed tube
1a; R = H
1h; R = CH3,
1i: OCH3
1j; C(CH3)3
R
R
2a; R = H
3a; R = H
2h; R = CH3,
2i: OCH3
3h; R = CH3,
3i: OCH3
2j; C(CH3)3
3j; C(CH3)3
Scheme 3. Reduction of substituted biphenyls (1a) and (1h–1j) by using
Al powder in the presence of Pt/C.
4. Conclusion
In conclusion, we have developed an efficient and
practical method of hydrogenation of aromatic compounds
using Al powder with a noble metal catalyst in water under
mild reaction conditions. Without using any organic
solvent, Al powder with Pd/C is effective for the selective
hydrogenation of one benzene ring and Al powder with Pt/
C gives the complete hydrogenation of aromatic com-
pounds. The hydrogenation product yields strongly
depended upon the temperature, volume of water and
amount of the metal catalysts used. Our hydrogenation
process is operationally simple and no harsh reaction
conditions (i.e. elevated temperatures, high pressures, a
hydrogen atmosphere, an inert gas atmosphere or special
apparatus) are required.
Table 5
Reduction of substituted biphenyls (1a) and (1h–1j) by using Al powder
in the presence of Pt/Ca,b
.
Entry
Substrate (1)
Yield [%]c
2
3
Recovery 1
1
2
3
4
H
–
100
83d
23d
45d
–
6
8
7
CH3
11
30
48
OCH3
C(CH3)3
a
Substrate: 20 mg (0.13 mmol), co-catalyst: 4.5 mol% (metal), Al
powder: 100 mg (500 wt%), H2O: 0.5 mL.
b
Conditions: temperature: 80 8C, time: 12 h.
The yields were determined by GLC.
c
d
cis- and trans-isomers were obtained.
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[14] P.N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic
Acknowledgement
Press, New York, 1979, p. p175.
[15] S. Nishimura, Handbook of Heterogenious Catalytic Hydrogenation for
Organic Synthesis, Wiley, New York, 2001, p. 414.
[16] E.L. Muetterties, J.R. Bleeke, Acc. Chem. Res. 12 (1979) 324–331.
This work was performed under the Cooperative
Research Program of the ‘‘Network Joint Research Centre
for Materials and Devices (Institute for Materials Chem-
istry and Engineering, Kyushu University)’’.
´
[17] A.F. Borowski, S. Sabo-Etienne, B. Chaudret, J. Mol. Catal. A 174 (2001)
69–79.
[18] M. Freifelder, Practical Catalytic Hydrogenation, Wiley-Interscience,
1971.
[19] P. Rylander, Catalytic Hydrogenation in Organic Syntheses, Academic
Press, 1979.
[20] S. Nishimura, G. Takagi, Catalytic Hydrogenation Application to Organic
Syntheses, Tokyo Kagaku Doujinn, 1987.
Appendix A. Supplementary data
[21] T. Tsukinoki, T. Kanda, G.-B. Liu, H. Tsuzuki, M. Tashiro, Tetrahedron
Lett. 41 (2000) 5865–5868.
Supplementary data associated with this article can be
found, in the online version, at http://dx.doi.org/10.1016/
j.crci.2013.09.013.
[22] T. Maegawa, A. Akashi, K. Yaguchi, Y. Iwasaki, M. Shigetsura,
Y. Monguchi, H. Sajiki, Chem. Eur. J. 15 (2009) 6953–6963.
[23] Y. Monguchi, Y. Fujita, S. Hashimoto, M. Ina, T. Takahashi, R. Ito,
K. Nozaki, T. Maegawa, H. Sajiki, Tetrahedron 67 (2011) 8628–8634.
[24] T. Takahashi, M. Yoshimura, H. Suzuka, T. Maegawa, Y. Sawama,
Y. Monguchi, H. Sajiki, Tetrahedron 68 (2012) 8293–8299.
[25] Y. Gong, P. Zhang, X. Xu, Yi. Li, H. Li, Y. Wang, J. Catal. 297 (2013) 272–
280.
[26] C.H. Yen, H.W. Lin, C.-S. Tan, Catal. Today 174 (2011) 121–126.
[27] P.T. Anastas, J.C. Warner, Green Chemistry, Theory and Practice, Oxford
University Press, New York, 1998.
[28] C.-H. Li, T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley
and Sons, Inc., New York, 1997, p. 309.
[29] A. Lubineau, J. Auge, Y. Queneau, Synthesis 8 (1994) 741–760.
[30] C.-J. Li, Chem. Rev. 93 (1993) 2023–2035.
[31] H. Suzuki, H. Tashiro, K. Ishimoto, G.K.S. Prakash, G.A. Olah, M. Tashiro,
Jpn. J. Deuterium. Sci. 12 (2006) 25–31.
[32] A.-M. Simion, T. Arimura, C. Simion, C. R. Chimie 16 (2013) 476–481.
[33] K. Sakanishi, M. Ohira, I. Mochida, H. Okazaki, M. Soeda, Bull. Chem. Soc.
Jpn. 62 (1989) 3994–4001.
[34] M. Minabe, K. Suzuki, J. Org. Chem. 40 (1975) 1298–1302.
[35] J.M.L. Cameron, J.W. Cook, W. Graham, J. Chem. Soc. (1945) 286–288.
[36] E.A. Garlock Jr., E. Mosettig, J. Am. Chem. Soc. 67 (1945) 2255–2259.
[37] H. Suzuki, K. Ishimoto, H. Tashiro, G.K.S. Prakash, G.A. Olah, M. Tashiro,
Jpn. J. Deuterium. Sci. 12 (2006) 7–18.
References
[1] H.A. Smith, in: P.H. Emmett (Ed.), Catalysis, Vol. 5, Reinhold, New York,
1957, pp. 179–181.
[2] H. Adkins, Reactions of Hydrogen with Organic Compounds over
Copper–Chromium Oxide and Nickel Catalysts, University Wisconsin
Press, Madison, WI, USA, 193756–62.
[3] M.K. Akhmedli, Zh. Obshch. Khim. 17 (1947) 224–230.
[4] M.K. Akhmedli, Zh. Obshch. Khim. 19 (1949) 462–467.
[5] R. Adams, J.R. Marshall, J. Am. Chem. Soc. 50 (1928) 1970–1973.
[6] G. Gilman, G. Cohn, Adv. Catal. 9 (1957) 733–742.
[7] P.N. Rylander, Catalytic hydrogenation over Platinum Metals, Academic
Press, New York, 1967, p. 309.
[8] R.E. Lyle, J.J. Thomas, J. Org. Chem. 30 (1965) 1907–1909.
[9] G.W. Gribble, P.D. Lord, J. Skotnicki, S.E. Dietz, J.T. Eaton, J. Johnson,
J. Am. Chem. Soc. 96 (1974) 7812–7813.
[10] M. Yalpani, T. Lunow, R. Koester, Chem. Ber. 122 (1989) 687–693.
[11] M. Yalpani, Chem. Ber. 123 (1990) 983–987.
[12] R.A. Benkeser, R.E. Robinson, D.M. Sauve, O.H. Thomas, J. Am. Chem.
Soc. 77 (1955) 3230–3233.
[13] Z. Marcinow, P.W. Rabideau, J. Org. Chem. 55 (1990) 3812–3816.
Please cite this article in press as: Rayhan U, et al. Reduction of aromatic compounds with Al powder using noble metal
catalysts in water under mild reaction conditions. C. R. Chimie (2014), http://dx.doi.org/10.1016/j.crci.2013.09.013