Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze the preparation of N-sulfonylimines

Article abstract of DOI:10.1016/j.crci.2019.06.005

A new magnetic nanocatalyzed synthetic method for the synthesis of aldimines was evidenced. The reaction was carried out in a Schlenk tube under reflux conditions using various solvents and different nanomaterials as catalysts. In these reactions, an exce

Full text of DOI:10.1016/j.crci.2019.06.005

C. R. Chimie xxx (xxxx) xxx
Contents lists available at ScienceDirect
Comptes Rendus Chimie
www.sciencedirect.com
Preliminary communication/communication
Iron-based nanomaterials used as magnetic mesoporous
nanocomposites to catalyze the preparation of
N-sulfonylimines
,
Akram Ashouri a *, Saadi Samadi a, Behzad Nasiri a, Zohre Bahrami b
a Laboratory of Asymmetric Synthesis, Department of Chemistry, Faculty of Science, University of Kurdistan, 66177-15175, Sanandaj, Iran
b Faculty of Nanotechnology, Semnan University, Semnan, 35131-19111, Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
A new magnetic nanocatalyzed synthetic method for the synthesis of aldimines was evi-
denced. The reaction was carried out in a Schlenk tube under reflux conditions using
various solvents and different nanomaterials as catalysts. In these reactions, an excellent
yield of aromatic aldimines was obtained in the presence of silica-coated magnetic
nanomaterials. The prepared catalyst was also characterized by Fourier transform infrared
spectroscopy, scanning electron microscopy, nitrogen adsorption and desorption studies,
energy dispersive X-ray spectroscopy, and small-angle X-ray scattering spectroscopy. It
was shown that the magnetic nanocatalysts can be easily separated from the reaction
mixture using an external magnet and reused.
Received 4 March 2019
Accepted 26 June 2019
Available online xxxx
Keywords:
N-Sulfonylimines
Magnetic mesoporous nanomaterials
Aldimine
Fe3O4@MCM-41
Recyclability
© 2019 Académie des sciences. Published by Elsevier Masson SAS. All rights reserved.
1. Introduction
activity of the nitrogen atom of sulfonamide and the diffi-
culty in the removal of the produced water have limited the
Currently, electron-deficient imines such as sulfonyli-
mines are well known to be important as key intermediates
in various chemical reactions [1,2]. Owing to the applica-
bility of these compounds as anticancer agents, their anti-
inflammatory nature, and their antibacterial and anti-
fungal behavior, they are also known to be important for
biological processes [3]. Owing to their electrophilic nature,
relative stability, and reactivity, these electron-deficient
imines have been used in the preparation of several
important nitrogen-containing compounds [4e6]. Thus,
the development and application of suitable methods for
imine synthesis have attracted much attention in recent
years.
use of this method [7e9]. To suppress this limitation and
increase the efficiency, various methods in the presence of
Lewis and Brønsted acids or metal oxides are being devel-
oped [10], with some of these suffering from harsh reaction
conditions, use of toxic materials, long reaction times, and
use of high loading.
Magnetite-based nanomaterials have been used as cat-
alysts for a very wide range of catalytic processes and
organic transformations such as coupling reactions
[11e13], CeH activation [14], oxidation reactions [15],
reduction reactions [16], and synthesis of heterocyclic
compounds [17,18]. Therefore, multifunctional nano-
particles are in high demand because of their wide-ranging
applications in the field of catalysis. In addition, magnetite
nanoparticles are highly desirable for catalytic activity, but
under reflux conditions, some aggregation can occur
[19,20].
The most widely used and direct method for the prep-
aration of an N-sulfonylimine involves the condensation of
an aldehyde with sulfonamide, but the low nucleophilic
Despite the availability of numerous procedures for the
synthesis of imines, the design and development of a new
* Corresponding author.
E-mail address: a.ashouri@uok.ac.ir (A. Ashouri).
https://doi.org/10.1016/j.crci.2019.06.005
1631-0748/© 2019 Académie des sciences. Published by Elsevier Masson SAS. All rights reserved.
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005

2
A. Ashouri et al. / C. R. Chimie xxx (xxxx) xxx
efficient method for the synthesis of aldimines that are
more facile and economically advantageous are still of in-
terest. Herein, we attempted to introduce a simple, clean,
and efficient process to synthesize aldimines using silica-
coated magnetic nanoparticles.
nitrogen atmosphere. The reaction mixture was stirred for
1 h at 100 ꢀC. Then, the silica-coated magnetic nano-
particles were separated using a simple magnet. The solu-
tion of the reaction-separated system was transferred into a
round-bottomed flask. After the organic phase was evap-
orated under reduced pressure, the obtained crude product
was purified by recrystallization from ethyl acetate and n-
hexane, affording the pure product in high yield (up to
98%).
2. Experimental
2.1. Materials
N-(4-Chlorobenzylidene)-4-methylbenzenesulfona-
All of the chemicals were obtained from SigmaeAldrich
or Merck and were used without purification. The reaction
progress was monitored by thin-layer chromatography
(GF254). Fourier transform infrared (FT-IR) (KBr) spectra
were recorded using a Bruker Vector 22 FT-IR spectro-
photometer. The 1H NMR and 13C NMR spectra were
recorded using a Bruker AVIII HD-500 MHz instrument
using tetramethylsilane (TMS) as the internal standard.
mide (Table 3, entry 1) mp: 175e179 ꢀC, 1H NMR (500 MHz,
CDCl3)
(2H, d, J ¼ 8.5 Hz), 7.86 (2H, d, J ¼ 8.5 Hz), 7.88 (2H, d, J ¼
8.3 Hz), 8.99 (1H, s); 13C NMR (125 MHz, CDCl3)
(ppm):
d
(ppm): 2.43 (3H, s), 7.35 (d, J ¼ 8.1 Hz, 2H), 7.46
d
168.6, 144.8, 141.4, 134.8, 132.3, 130.8, 129.8, 129.5, 128.1,
21.6.
N-(4-Methylbenzylidene)-4-methyl-benzenesulfona-
mide (Table 3, entry 6) mp: 116e118 ꢀC. 1H NMR (500 MHz,
CDCl3)
d
(ppm): 8.99 (s, 1 H), 7.89 (d, J ¼ 7.5 Hz, 2 H), 7.82 (d,
2.2. Synthesis of different catalysts
J ¼ 7.4 Hz, 2 H), 7.34 (d, J ¼ 7.49 Hz, 2 H), 7.29 (d, J ¼ 7.43 Hz,
2 H), 2.43 (s, 3 H), 2.42 (s, 3 H); 13C NMR (125 MHz, CDCl3)
The different nanomaterials were synthesized according
d (ppm): 168.9, 145.3, 143.4, 134.4, 130.4 (2C), 128.9 (2C),
to reports in the literature [21e24].
128.8, 128.7 (2C), 127.0 (2C), 20.9, 20.6.
N-(4-Methoxybenzylidene)-4-methyl-benzenesulfo-
2.2.1. Preparation of MCM-41 mesoporous silica
namide (Table 3, entry 8) mp: 128e129 ꢀC, 1H NMR
MCM-41 mesoporous silica samples were prepared
using a general method [25,26]. The water solution of
cetyltrimethylammonium bromide (142 mg, 0.39 mmol)
was added to diethanolamine (9.46 mg, 0.09 mmol) and
stirred at 40 ꢀC for at least 30 min, followed by the addition
of tetraethyl orthosilicate (333 mg, 1.6 mmol) dropwise
within 2 min. After 2 h, the solution was cooled to room
temperature, and a white residue powder precipitate was
obtained that was then centrifuged and washed with
ethanol and distilled water. The surfactant cetyl-
trimethylammonium bromide was extracted from the ob-
tained mesoporous materials by refluxing with ethanol and
a small amount of concentrated HCl. The final product was
centrifuged and washed with ethanol several times.
(500 MHz, CDCl3)
4 H), 7.32 (d, J ¼ 7.7 Hz, 2 H), 6.96 (d, J ¼ 8.2 Hz, 2 H), 3.87 (s,
3 H), 2.42 (s, 3 H); 13C NMR (125 MHz, CDCl3)
(ppm):
168.1, 164.3, 143.2, 134.7, 132.6 (2C), 128.7 (2C), 126.8 (2C),
124.2, 113.6 (2C), 54.6, 20.5.
d
(ppm): 8.94 (s, 1 H), 7.87 (d, J ¼ 8 Hz,
d
3. Results and discussion
Initially, in a sealed Schlenk tube under nitrogen at-
mosphere, the reaction of p-chlorobenzaldehyde (1a) and
p-toluenesulfonamide (2) was selected as a model reaction
in refluxing toluene; but after 24 h, product 3a was ob-
tained which was not the desired product. Following the
reports in the literature, we attempted to carry out the
condensation reaction in the presence of catalysts that act
as Lewis acids and dehydrating reagents. For this purpose,
we carried out the reaction in the presence of several metal
oxide nanocatalysts. The obtained results are shown in
Table 1. According to entries 2e6, the reaction proceeded in
the presence of Al2O3, TiO2, MgO, SiO2, and Fe3O4 metal
oxide nanoparticles with moderate yields. On the other
hand, owing to its unique properties such as narrow pore
size distribution, ultrahigh surface area, well-defined pore
structure, and thermal stability, MCM-41 mesoporous silica
has been used in several catalytic organic reactions
[27e32]. A review of the literature showed that the use of
MCM-41 mesoporous silica for the synthesis of aldimines
has not been reported. It occurred to us that this class of
nanomaterials may be a catalyst for this reaction. When we
used MCM-41, the reaction yield increased to 67% (entry 7).
To enhance the efficiency of MCM-41 mesoporous silica, we
decided to use the silica-coated magnetic nanoparticles
denoted as Fe3O4@MCM-41 (entry 8). When the reaction
was carried out in the presence of Fe3O4@MCM-41, the
desired product was obtained with the yield of 98% (entry
10). We also used K10 montmorillonite clays as the catalyst
2.2.2. Preparation of nanomagnetic Fe3O4
Nanomagnetic Fe3O4 was prepared using the typical
solvothermal method. A round-bottomed flask containing
ethylene glycol (30 mL) was filled with ferric chloride
hexahydrate (1.48 g, 5.5 mmol) and sodium acetate (2.62 g,
32 mmol). The mixture was heated for 8 h at 200 ꢀC in an
autoclave and then cooled to room temperature. The black
nanomagnetic Fe3O4 was separated using an external
magnet, washed with deionized water several times, and
ꢀ
dried in an oven at 60 C overnight [25,26].
2.2.3. Preparation of Fe3O4@MCM-41
The procedure for the preparation of Fe3O4@MCM-41
was the same as that for nanomagnetic Fe3O4 except that in
the first step, the prepared MCM-41 (2.0 g) was added to
the reaction mixture [29].
2.2.4. General procedure for the synthesis of products
To a Schlenk tube filled with Fe3O4@MCM (15 mg) and
toluene (0.5 mL), aldehyde (0.12 mmol) and p-toluene-
sulfonamide (17.12 mg, 0.1 mmol) were added under
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005

A. Ashouri et al. / C. R. Chimie xxx (xxxx) xxx
3
Table 1
Effect of various nanocatalysts on the model reaction.
Entrya
Type of nanocatalysts
Loading of nanocatalysts (mg)
Yield (%)b
1
e
e
e
2
3
4
5
6
7
8
9
10
11
12
13
Al2O3
TiO2
MgO
Fe3O4
15
15
15
15
15
15
15
15
5
52
40
55
62
67
98
40
65
80
75
58
SiO2
MCM-41
Fe3O4@MCM-41
K10
Fe3O4@MCM-41
Fe3O4@MCM-41
Fe3O4@MCM-41
Fe3O4@MCM-41
10
20
25
a
Reaction conditions: p-chlorobenzaldehyde (0.12 mmol), p-toluenesulfonamide (0.1 mmol), toluene (0.5 mL), and nanocatalysts.
Isolated yield.
b
under these conditions; but after 1 h, the yield was lower
1e3). When dichloromethane, chloroform, diethyl ether,
and dimethyl sulfoxide were used, the desired aldimine
was produced in low to moderate yields (entries 4e7),
whereas the use of toluene as solvent promoted the reac-
tion with an extremely high yield (entry 8).
After achieving optimum conditions, the scope of the
reaction was evaluated by applying different aldehydes.
Several aromatic and aliphatic aldehydes were used, as
presented in Table 3. It was found that aromatic alde-
hydes with an electron-donating group reacted, as did
those with electron-withdrawing groups. An aromatic
than that obtained using other nanocatalysts (entry 9).
Subsequently, we optimized other parameters that affect
the reaction. In particular, the effect of different loading
amounts of Fe3O4@MCM-41 was investigated (entries
10e13). However, it was found that the best yield was
achieved using 15 mg of silica-coated magnetic
nanocatalysts.
As presented in Table 2, the effect of the solvent was also
observed for this reaction. No product was observed using
tetrahydrofuran, 1,4-dioxane ,and acetonitrile (entries
Table 2
Effect of various solvents on the model reaction.
Entrya
Solvent
Yield (%)b
1
2
3
4
5
6
7
8
1,4-Dioxane
Tetrahydrofuran
Acetonitrile
Dichloromethane
Chloroform
Diethyl ether
Dimethyl sulfoxide
Toluene
e
e
e
10
20
35
38
98
a
Reaction condition: p-chlorobenzaldehyde (0.12 mmol), p-toluenesulfonamide (0.1 mmol), solvent (0.5 mL), and Fe3O4@MCM-41 (15 mg).
Isolated yield.
b
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005

4
A. Ashouri et al. / C. R. Chimie xxx (xxxx) xxx
Table 3
Reaction scope.
Entrya
R
Yield (%)b
Mp (ꢀC)
Mp (ꢀC)c
1
2
3
4
5
6
7
8
p-Cl-Phenyl
o-Cl-Phenyl
m-Cl-Phenyl
p-F-Phenyl
p-NO2-Phenyl
p-CH3-Phenyl
p-Br-Phenyl
p-OCH3-Phenyl
oeOCH3-Phenyl
p-CF3-Phenyl
-Phenyl
-Naphthyl
-Anthracyl
-Benzyl
-Hexyl
-Propenyl
98
82
92
88
85
90
92
87
85
90
86
89
175e179
134e137
84e88
172e173 [33]
131e132 [34]
98 [34]
129e130
203e207
113e115
190e193
129e130
111e114
154e156
79e82
117e118 [35]
162e170 [35]
116e118 [36]
198e199 [37]
128e129 [35]
111e113 [38]
159e160 [39]
105e108 [35]
142e144 [40]
214e217 [41]
e
9
10
11
12
13
14
15
16
140e144
199e204
e
82
Oily mixture
Oily mixture
Oily mixture
e
e
e
e
a
Reaction conditions: aldehyde (0.12 mmol), p-toluenesulfonamide (0.1 mmol), toluene (0.5 mL), and Fe3O4@MCM-41 (15 mg).
Isolated yield.
Reported Mp.
b
c
aldimine substituted with bulky aryl groups was synthe-
morphology of the samples was examined using a ZEISS
SIGMA VP field emission scanning electron microscope (FE-
SEM) equipped with a field emission gun and an energy
dispersive (EDS) detector. The surface areas were calculated
according to the BrunauereEmmetteTeller (BET) equation
and the pore size distribution was calculated using the
BarretteJoynereHalenda (BJH) equation. Elemental anal-
ysis was performed quantitatively using an Infinite 200
PRO NanoQuant instrument (Tecan, Switzerland). The
nanoscale density differences were evaluated by small-
angle X-ray scattering (SAXS) spectroscopy.
sized in high yields (entries 12 and 13). As expected, ar-
omatic aldehydes reacted better than the aliphatic
aldehydes (entries 14e16). In nearly all of the investigated
reactions, the conversion was over 95% under the reaction
conditions.
3.1. Characterization of materials
The prepared materials were characterized using a
Bruker Vector 22 FT-IR spectrophotometer. The surface
Fig. 1. FT-IR spectra of (a) MCM-41, (b) Fe3O4, and (c) Fe3O4@MCM-41.
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005

A. Ashouri et al. / C. R. Chimie xxx (xxxx) xxx
5
Fig. 2. SEM images of (a) Fe3O4, (b) MCM-41, and (c) Fe3O4@MCM-41.
Table 4
Textural properties of MCM-41 and Fe3O4@MCM-41 nanoparticles.
Sample
Specific surface area Pore volume
Pore
diameter (Dp)
(nm)
(SBET) (m2 gꢁ1
)
(Vp) (cm3 gꢁ1
)
MCM-41
nanoparticles
Fe3O4@MCM-41 690
nanoparticles
817
1.068
0.873
2.42
2.42
3.2. Composition and morphology of Fe3O4, MCM-41, and
Fe3O4@MCM-41
The FT-IR spectra of the prepared MCM-41, Fe3O4, and
Fe3O4@MCM-41 are shown in Fig. 1. The asymmetric and
symmetric stretching vibrations of the siloxane groups
(SieOeSi) of MCM-41 are ascribed to the bands at 1074 and
796 cmꢁ1 that are observed to be unchanged in
Fig. 3. N2 adsorption/desorption isotherm of MCM-41 and Fe3O4@MCM-41
nanoparticles.
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005

6
A. Ashouri et al. / C. R. Chimie xxx (xxxx) xxx
Fig. 4. EDX spectrum of Fe3O4@MCM-41.
microscopy (SEM) and are shown in Fig. 2. Bare Fe3O4
nanoparticles have a quasi-spherical shape with a hetero-
geneous surface and slight aggregation. The shape of the
resulting silica-coated magnetic nanoparticles was also
spherical after grafting on MCM-41. These results indicated
that Fe3O4 nanoparticles were successfully grafted on the
MCM-41 nanoparticles without considerable changes dur-
ing the functionalization process.
N2 adsorptionedesorption isotherms and pore size
distributions of MCM-41 and Fe3O4@MCM-41 silica-coated
magnetic nanoparticles are shown in Fig. 3. The isotherms
and pore size distributions of MCM-41 magnetic meso-
porous silica and corresponding silica-coated magnetic
nanoparticles are nearly same, indicating that the pore
structures of the MCM-41 mesoporous silica were still
preserved even after the grafting of Fe3O4 nanoparticles on
the MCM-41 mesoporous silica. The textural properties of
MCM-41 and Fe3O4@MCM-41 nanoparticles are summa-
rized in detail in Table 4. It is clear that the surface area and
pore volume of silica-coated magnetic nanoparticles were
lower than those of the MCM-41 mesoporous silica; how-
ever, the surface areas and large pore volumes of the
Fe3O4@MCM-41 nanoparticles are still high.
Fig. 5. SAXS patterns of MCM-41 and Fe3O4@MCM-41 nanoparticles.
Fig. 4 shows the energy-dispersive X-ray (EDX) spec-
trum of the obtained Fe3O4@MCM-41 nanoparticles that
reveals the presence of Fe, O, and Si elements, confirming
that MCM-41 was successfully coated by magnetite
nanoparticles.
The small angle X-ray scattering (SAXS) patterns of
MCM-41 and silica-coated magnetic nanoparticles are
presented in Fig. 5 and are in good agreement with those
Fe3O4@MCM-41. The strong absorption band related to the
FeeO bond observed at approximately 586 cmꢁ1 in the
Fe3O4 and Fe3O4@MCM-41 spectra confirms the prepara-
tion and the presence of magnetite nanoparticles,
respectively.
The surface morphologies of Fe3O4, MCM-41, and
Fe3O4@MCM-41 were observed by scanning electron
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005

A. Ashouri et al. / C. R. Chimie xxx (xxxx) xxx
7
Scheme 1. Proposed mechanism for the synthesis of aldimine derivatives in the presence of silica-coated magnetic nanoparticles.
reported in the literature [42]. The SAXS pattern of the
silica-coated magnetic nanoparticles was almost identical
to that of the corresponding mesoporous silica. This result
also supports the conclusion that the pore structures of
mesoporous silica were preserved even after the grafting of
Fe3O4 nanoparticles.
3.3. Proposed mechanism
A proposed mechanism for the synthesis of aldimine
derivatives in the presence of silica-coated magnetic
nanoparticles is shown in Scheme 1. After activation of the
aldehyde carbonyl group by Fe3O4@MCM-41, the nucleo-
philic attack of the nitrogen atom of sulfonamide occurred,
Fig. 6. Effect of catalyst recycling on the yield of product 3a.
and an intermediate (І) was formed. Consequently, the
aldimine product 3a was prepared by the dehydration of
the intermediate (І).
4. Conclusions
In this work, a simple and new synthetic method of
silica-coated magnetic nanoparticles via the condensation
of aldehyde and p-toluenesulfonamide using silica-coated
iron-based magnetic nanoparticles was introduced. The
synthesis of aldimines was carried out in a Schlenk tube
3.4. Recyclability and reusability of the catalyst
Recyclability and reusability of the catalyst are impor-
tant for designing a new synthesis method. Therefore, the
reusability of the silica-coated magnetic nanoparticles was
also evaluated for the condensation reaction. The conver-
sion and yield of the reaction were over 90% and 83%,
respectively, until five cycles, demonstrating that the cat-
alytic activity of the silica-coated magnetic nanoparticles
was preserved without a significant loss (see Fig. 6). After
each reaction, magnetic nanocatalysts were simply sepa-
rated by an external magnet, washed with ethanol, dried
under reduced pressure and reused. The FT-IR spectrum
and SEM image of the recycled catalyst confirmed that the
structure of the catalyst was maintained.
that can be easily handled in comparison with
a
DeaneStark apparatus. The excellent yield of aromatic
aldimines, short reaction time, facile separation, reusability
of catalysts, and lack of catalyst pollution in the products
are the prominent advantages of this method.
Acknowledgements
We are grateful to the University of Kurdistan, Iran
Research Councils for the support of this work.
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005

8
A. Ashouri et al. / C. R. Chimie xxx (xxxx) xxx
[20] W. Xie, X. Zang, Food Chem. 194 (2016) 1283e1292.
Appendix A. Supplementary data
[21] B. Li, X. Wang, M. Yan, L. Li, Mater. Chem. Phys. 78 (2003) 184e188.
[22] F. Liu, M.M. Abed, K. Li, J. Membr. Sci. 366 (2011) 97e103.
[23] C.H. Kwon, J.H. Kim, I.S. Jung, H. Shin, K.H. Yoon, Ceram. Int. 29
(2003) 851e856.
[24] Z.-X. Tang, L.-E. Shi, Ecletica Quim. 33 (2008) 15e20.
[25] W. Xie, Y. Han, H. Wang, Renew. energ. 125 (2018) 675e681.
[26] S. Luo, G. Fan, M. Luo, J. Li, G. Song, J CO2 UTIL 14 (2016) 23e30.
[27] S.C. Tang, I.M. Lo, Water Res. 47 (2013) 2613e2632.
[28] A. Yan, X. Liu, G. Qiu, H. Wu, R. Yi, N. Zhang, J. Xu, J. Alloy. Comp. 458
(2008) 487e491.
Supplementary data to this article can be found online
at https://doi.org/10.1016/j.crci.2019.06.005.
References
[1] M.E. Belowich, J.F. Stoddart, Chem. Soc. Rev. 41 (2012) 2003e2024.
[2] A. Kajal, S. Bala, S. Kamboj, N. Sharma, V. Saini, J. Catal. 2013 (2013).
[3] A.T. Baviskar, U.C. Banerjee, M. Gupta, R. Singh, S. Kumar,
M.K. Gupta, S. Kumar, S.K. Raut, M. Khullar, S. Singh, Bioorg. Med.
Chem. 21 (2013) 5782e5793.
[29] S.V. Kolotilov, O. Shvets, O. Cador, N. Kasian, V.G. Pavlov, L. Ouahab,
V.G. Ilyin, V.V. Pavlishchuk, J. Solid State Chem. 179 (2006)
2426e2432.
ꢀ
ꢀ
[4] J.L. Garcia Ruano, J. Aleman, M. Belen Cid, A. Parra, Org. Lett. 7 (2005)
[30] M. Vallet-Regi, A. Ramila, R. Del Real, J. Perez-Pariente, Chem. Mater.
179e182.
13 (2001) 308e311.
ꢀ
[5] A. Vass, J. Dudas, R.S. Varma, Tetrahedron Lett. 40 (1999)
[31] K. Chaudhari, T. Das, P. Rajmohanan, K. Lazar, S. Sivasanker,
A. Chandwadkar, J. Catal. 183 (1999) 281e291.
[32] X. Zhao, G. Lu, X. Hu, Microporous Mesoporous Mater. 41 (2000)
37e47.
[33] C.-Y. Chen, H.-X. Li, M.E. Davis, Microporous Mater. 2 (1993) 17e26.
[34] S. Samadi, K. Jadidi, B. Khanmohammadi, N. Tavakoli, J. Catal. 340
(2016) 344e353.
4951e4954.
[6] L. Wu, X. Yang, X. Wang, F. Yan, J. Sulfur Chem. 31 (2010) 509e513.
[7] S. Nakamura, M. Hayashi, Y. Hiramatsu, N. Shibata, Y. Funahashi,
T. Toru, J. Am. Chem. Soc. 131 (2009) 18240e18241.
[8] S. Kobayashi, Y. Mori, J.S. Fossey, M.M. Salter, Chem. Rev. 111 (2011)
2626e2704.
[9] R.N. Ram, A.A. Khan, Synth. Commun. 31 (2001) 841e846.
[10] J.H. Wynne, S.E. Price, J.R. Rorer, W.M. Stalick, Synth. Commun. 33
(2003) 341e352.
[11] Y. Long, K. Liang, J. Niu, X. Tong, B. Yuan, J. Ma, New J. Chem. 39
(2015) 2988e2996.
[35] S. Samadi, A. Ashouri, M. Ghambarian, RSC Adv.
7 (2017)
19330e19337.
[36] T.S. Jin, M.J. Yu, L.B. Liu, Y. Zhao, T.S. Li, Synth. Commun. 36 (2006)
2339e2344.
[37] R. Patel, V.P. Srivastava, L.D.S. Yadav, Adv. Synth. Catal. 352 (2010)
1610e1614.
[38] D. Huang, X. Wang, X. Wang, W. Chen, X. Wang, Y. Hu, Org. Lett. 18
(2016) 604e607.
[12] W. Li, Y. Tian, B. Zhang, L. Tian, X. Li, H. Zhang, N. Ali, Q. Zhang, New
J. Chem. 39 (2015) 2767e2777.
[13] J. Niu, F. Wang, X. Zhu, J. Zhao, J. Ma, RSC Adv.
4 (2014)
37761e37766.
[39] A. Zare, F. Bahrami, M. Merajoddin, M. Bandari, A.R. Moosavi-Zare,
M.A. Zolfigol, A. Hasaninejad, M. Shekouhy, M.H. Beyzavi,
V. Khakyzadeh, Org. Prep. Proced. Int. 45 (2013) 211e219.
[40] M.D. Hopkins, K.A. Scott, B.C. DeMier, H.R. Morgan, J.A. Macgruder,
A.A. Lamar, Org. Biomol. Chem. 15 (2017) 9209e9216.
[41] A.K. Bhattacharya, K.C. Rana, C. Pannecouque, E. De Clercq, Chem-
MedChem 7 (2012) 1601e1611.
[14] R. Sharma, S. Dutta, S. Sharma, Dalton Trans. 44 (2015) 1303e1316.
[15] L. Lykke, C. Rodríguez-Escrich, K.A. Jørgensen, J. Am. Chem. Soc. 133
(2011) 14932e14935.
[16] T.C. Nugent, M. El-Shazly, Adv. Synth. Catal. 352 (2010) 753e819.
[17] A.V. Kel'in, A.W. Sromek, V. Gevorgyan, J. Am. Chem. Soc. 123 (2001)
2074e2075.
[18] Y.-L. Shi, M. Shi, Org. Biomol. Chem. 5 (2007) 1499e1504.
[19] W. Xie, J. Wang, Energy Fuel. 28 (2014) 2624e2631.
[42] C.-J. Wang, M. Shi, J. Org. Chem. 68 (2003) 6229e6237.
Please cite this article as: A. Ashouri et al., Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze
the preparation of N-sulfonylimines, Comptes Rendus Chimie, https://doi.org/10.1016/j.crci.2019.06.005