Design and characterization of nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a novel, heterogeneous and reusable catalyst for the condensation of arylaldehydes with β-naphthol and alkyl carbamates

Article abstract of DOI:10.1007/s11164-015-2154-7

In this research, nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a new and efficient Br?nsted acidic ionic liquid supported on silica has been synthesized, and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, thermogravimetric, differential thermal gravimetric, X-ray diffraction, and energy-dispersive X-ray spectroscopy spectra. The presented silica-supported ionic liquid has been applied as a highly effective, heterogeneous, easy regenerable, and reusable catalytic system for the solvent-free condensation of arylaldehydes with β-naphthol and alkyl carbamates leading to α-carbamatoalkyl-β-naphthols. Once the nanocatalyst was regenerated and reused, no significant loss of its activity was observed. Graphical Abstract: Design and characterization of nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a novel, heterogeneous and reusable catalyst for the condensation of arylaldehydes with β-naphthol and alkyl carbamates.[Figure not available: see fulltext.]

Full text of DOI:10.1007/s11164-015-2154-7

Res Chem Intermed
DOI 10.1007/s11164-015-2154-7
Design and characterization of nano-silica-bonded 3-n-
propyl-1-sulfonic acid imidazolium chloride {nano-SB-
[PSIM]Cl} as a novel, heterogeneous and reusable
catalyst for the condensation of arylaldehydes
with b-naphthol and alkyl carbamates
Abdolkarim Zare1 Maria Merajoddin1
•
•
Ahmad Reza Moosavi-Zare2 Mahmoud Zarei3
M. Hassan Beyzavi4 Mohammad Ali Zolfigol3
•
•
•
Received: 5 March 2015 / Accepted: 24 June 2015
Ó Springer Science+Business Media Dordrecht 2015
Abstract In this research, nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium
chloride {nano-SB-[PSIM]Cl} as a new and efficient Brønsted acidic ionic liquid sup-
ported on silica has been synthesized, and characterized using Fourier transform infrared
spectroscopy, scanning electron microscopy, transmission electron microscopy, ther-
mogravimetric, differential thermal gravimetric, X-ray diffraction, and energy-dispersive
X-ray spectroscopy spectra. The presented silica-supported ionic liquid has been applied
as a highly effective, heterogeneous, easy regenerable, and reusable catalytic system for
the solvent-free condensation of arylaldehydes with b-naphthol and alkyl carbamates
leading to a-carbamatoalkyl-b-naphthols. Once the nanocatalyst was regenerated and
reused, no significant loss of its activity was observed.
Graphical Abstract Design and characterization of nano-silica-bonded 3-n-propyl-1-
sulfonic acid imidazolium chloride {nano-SB-[PSIM]Cl} as a novel, heterogeneous and
reusable catalyst for the condensation of arylaldehydes with b-naphthol and alkyl
carbamates.
Electronic supplementary material The online version of this article (doi:10.1007/s11164-015-2154-7)
contains supplementary material, which is available to authorized users.
&
Abdolkarim Zare
abdolkarimzare@pnu.ac.ir; abdolkarimzare@yahoo.com
1
2
Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran
Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, 6541835583 Asadabad,
Iran
3
4
Faculty of Chemistry, Bu-Ali Sina University, 6517838683 Hamedan, Iran
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St.,
Cambridge MA 02138, USA
123

A. Zare et al.
Keywords Nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride
{nano-SB-[PSIM]Cl} Á Silica-supported Brønsted acidic ionic liquid Á
Arylaldehyde Á b-Naphthol Á Alkyl carbamate Á a-Carbamatoalkyl-b-naphthol
Introduction
As catalysts for organic reactions and green reaction media, ionic liquids (ILs) have
been applied for many interesting transformations. They have various distinct
properties such as non-volatility, a wide liquid-state temperature range, non-
flammability, very low vapor pressures, reasonable thermal and chemical stability,
excellent ionic conductivities, electrochemical stability, a large electrochemical
window, recyclability as well as reusability, eco-friendly, tunable hydrophobicity,
and favorable solvation behavior [1–14]. Because of their operational efficacy and
selectivity along with their green nature, among different types of ILs, Brønsted
acidic ones have shown the potential for ,, progress of environmental friendly acid-
catalyzed organic reactions [5–14]. On the other hand, lately, heterogenization of
ILs by decorating them on solid supports has grasped an ever increasing attention.
The immobilization of IL catalysts can extensively expand their applications in
addition to the advantages of their homogeneous counterparts, their application,
handling, isolation, and reusing process make them superior to other catalysts. From
the economic point of view, it is highly favorable to minimize the amount of IL
applied in the potential transformations [15–21], and alternatively solid-supported
acidic ILs have been applied as remarkable heterogeneous catalysts for a myriad of
acid-catalyzed transformations [15–21].
The chemistry of nano-sized materials is a growing and effective field in the
modern technology. Nanocatalysts continue to attract attention for a variety of
research disciplines because of their different chemical and physical characteristics
once compared with bulk materials. The nano-sized particles maximize the surface
area exposed to the reagents facilitating more reactions to take place concurrently,
which, therefore, enhances the rate of the chemical reaction [22–27].
Multi-component reactions (MCRs) play a significant role in combinatorial
chemistry since they can synthesize desired products with better efficacy and atomic
123

Design and characterization of nano-silica-bonded…
economy in a single step from three or more starting materials. Furthermore, they
decrease energy consuming steps such as separation and purification of interme-
diates, and improve raw materials consumption. MCRs also present the advantage
of synthetic efficiency and simplicity compared with conventional chemical
reactions [28–31].
Structures holding a,c-amino-oxygenated motifs are significant in a variety of
biologically distinct natural products and potent pharmaceutical compounds such as
nucleoside antibiotics and HIV protease inhibitors like ritonavir and lipinavir [32,
33]. Derivatives of a-carbamatoalkyl-b-naphthol are considered as a class of a,c-
amino-oxygen containing systems. In addition, these structures can be easily
transformed into a-aminoalkyl-b-naphthols as a biologically important motif by
carbamate hydrolysis. For example, a-aminoalkyl-b-naphthol derivatives have
bradycardiac and hypotensive properties [34, 35]. One of the rational synthetic
approaches toward a-carbamatoalkyl-b-naphthols is the catalyzed condensation of
arylaldehydes with b-naphthol and alkyl carbamates [36–50].
Recently, we introduced sulfonic acid-functionalized imidazolium salts
(SAFIS) and quaternary ammonium salts as a new type of Brønsted acidic ILs
[9–14]. In these materials, SO3H functional groups have been bonded to positive
nitrogens (N?) for the first time. We applied them as highly efficient and
homogeneous catalysts for different organic transformations [9–14]. Although
these ILs efficiently catalyzed several organic reactions, recycling and reusing
the ILs were difficult. To overcome this drawback, we decided to heterogenize
this class of ILs by supporting them on solids. In this regard, we report in the
present work, nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chlo-
ride {nano-SB-[PSIM]Cl} as the first class of heterogenenized SAFIS (Fig. 1),
and fully characterize it by Fourier transform infrared spectroscopy (FT-IR),
scanning electron microscopy (SEM), transmission electron microscopy (TEM),
thermogravimetric (TG), differential thermal gravimetric (DTG), X-ray diffrac-
tion (XRD), and energy-dispersive X-ray spectroscopy (EDX) analysis. Encour-
aged by that, we utilize the heterogeneous SAFIS as a highly effective, easy
regenerable and reusable nanocatalyst for the solvent-free production of a-
carbamatoalkyl-b-naphthols through the condensation between arylaldehydes, b-
naphthol, and alkyl carbamates under relatively mild conditions (70 °C). In this
research, a helpful organic reaction is reported via the combination of
heterogeneous and solid-supported IL nanocatalyst under solvent-free and
relatively mild conditions, which represents an interesting approach toward the
so-called ‘‘ideal synthesis.’’
Fig. 1 The structure of nano-
silica-bonded 3-n-propyl-1-
sulfonic acid imidazolium
chloride
O
O Si
SO3H
O
N
N
Cl
Nano-SB-[PSIM]Cl
123

A. Zare et al.
Experimental
General
All starting materials were purchased from Merck or Fluka Chemical Companies.
The nano-silica gel for the preparation of nano-SB-[PSIM]Cl was synthesized by the
reported procedure [51]. For identification of known products, their melting points
and spectral data were compared with the reported data in the literature. Progress of
1
the reactions was monitored by TLC using silica gel SIL G/UV 254 plates. The H
NMR (400 MHz) and 13C NMR (100 MHz) were run on a Bruker Avance DPX FT-
NMR spectrometer (d in ppm). Melting points were recorded on a Bu¨chi B-545
apparatus in open capillary tubes. Thermal gravimetry (TG) and differential thermal
gravimetric (DTG) were analyzed by a Perkin Elmer (Model: Pyris 1). TG/DTG
analysis was done (25–600 °C, temperature increase rate of 10 °C min-1, nitrogen
atmosphere).
Procedure for the production of nano-silica-bonded 3-n-propyl-1-sulfonic
acid imidazolium chloride {nano-SB-[PSIM]Cl}
A mixture of imidazole (0.34 g, 5 mmol), (3-chloropropyl)triethoxysilane (1.125 g,
5 mmol) and toluene (15 mL) in a 50 mL round-bottomed flask connected to a
reflux condenser, was stirred for 12 h under reflux conditions. The obtained white
precipitate was filtered, washed with toluene (2 9 5 mL), and dried to give
intermediate II (Scheme 1). In the next step, the obtained intermediate II reacted
with silica gel (0.30 g, 5 mmol) in refluxed ethyl acetate (15 mL) for 8 h. The
formed precipitate was separated by centrifuging and decanting, washed by ethyl
acetate (2 9 5 mL), and dried to afford intermediate III. Subsequently, a solution of
chlorosulfonic acid (5 mmol) in chloroform (10 mL) was added dropwise to
Toluene
Reflux, 12 h
N
Si(OEt3)
HN
N
HN
+
Cl
Si(OEt)3
Si(OEt3)
Cl
(I)
ca
Sili
- HCl
N
N
Ethyl acetate, Reflux, 8 h
-3EtOH
(II)
N
O
O
O Si
O
O Si
ClSO3H
SO3H
O
N
N
N
CHCl3, 0 °C
Cl
2 h
(III)
(IV) (Nano-SB-[PSIM]Cl)
Scheme 1 The production of nano-SB-[PSIM]Cl
123

Design and characterization of nano-silica-bonded…
intermediate III at 0 °C (ice-water bath), and stirred for 2 h at this temperature. The
solvent was removed by centrifuging and decanting, and the residue was triturated
with chloroform (3 9 10 mL), and dried under powerful vacuum at 90 °C to give
nano-SB-[PSIM]Cl as a white precipitate in a 95 % yield.
General procedure for the production of a-carbamatoalkyl-b-naphthols
To a mixture of b-naphthol (0.144 g, 1 mmol), arylaldehyde (1 mmol) and alkyl
carbamate (1.3 mmol) in a test tube, was added nano-SB-[PSIM]Cl (0.01 g), and the
resulting mixture was stirred magnetically at 70 °C, and after solidification of the
reaction mixture with a small rod at that temperature. The mixture was cooled to room
temperature, then warm EtOAc (5 mL) was added and stirred for 1 min followed by
centrifugation and decanting to separate nano-SB-[PSIM]Cl (the silica-bonded IL is
not soluble in warm EtOAc, but the unreacted starting materials and the product are
soluble in it). The separated EtOAc was evaporated, and the solid residue was
recrystallized from hot EtOH (95 %) to give the pure a-carbamatoalkyl-b-naphthol.
Note The spectral data of a-carbamatoalkyl-b-naphthols have been given in the
Supplementary Material.
Results and discussion
Production of nano-SB-[PSIM]Cl (Scheme 1)
At first, imidazole reacted with (3-chloropropyl)triethoxysilane under to give I,
which transformed to II as a white precipitate by releasing HCl gas. In the next step,
II reacted with silica in ethyl acetate to afford III. Subsequently, by the reaction of
III with chlorosulfonic acid, nano-SB-[PSIM]Cl(IV) was produced as a white
precipitate.
Fig. 2 The FT-IR spectrum of nano-SB-[PSIM]Cl
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A. Zare et al.
Characterization of the nanocatalyst
The nanocatalyst structure was identified by FT-IR, SEM, TEM, TG, DTG, XRD,
and EDX analysis.
IR spectrum of nano-SB-[PSIM]Cl
The IR spectrum of the catalyst revealed a broad peak at 2500–3600 cm-1, which
could be related to O–H stretching of the SO3H group. Moreover, the two peaks
observed at 1046 and 1106 cm-1 corresponded to vibrational modes of N-SO2 and
O-SO2 bonds (Fig. 2).
Fig. 3 The SEM micrographs of nano-SB-[PSIM]Cl
123

Design and characterization of nano-silica-bonded…
SEM of the nanocatalyst
The SEM micrographs of the catalyst are shown in Fig. 3. As is clear from this Fig.,
the particles of nano-SB-[PSIM]Cl have not completely agglomerated, and the
particles were observed in nano-scale.
TEM of nano-SB-[PSIM]Cl
To further confirm the nanostructure of nano-SB-[PSIM]Cl, TEM measurements
were performed as shown in Fig. 4. The TEM micrograph proved the presence of
more or less spherical nanoparticles with a mean diameter of 12.0 nm.
TG and DTG of the nanocatalyst
The TG and DTG diagrams of the catalyst showed weight loss in one step at 325 °C
(Fig. 5).
XRD study of nano-SB-[PSIM]Cl
XRD pattern of nano-SB-[PSIM]Cl was investigated in a domain of 0–90 degree
(Fig. 6). As shown in this Fig., XRD patterns exhibited diffraction lines of a high
crystalline nature at about 2h & 9.6°, 12.1°, 19.5°, 20.2°, 22.8°, and 81.7°.
EDX of nano-SB-[PSIM]Cl
EDX of the obtained nanomaterials (Fig. 7) provided the presence of the expected
elements in the catalyst structure, namely carbon, oxygen, nitrogen, sulfur, chlorine,
and silicon.
Fig. 4 The TEM image of nano-SB-[PSIM]Cl
123

A. Zare et al.
°
Fig. 5 The TG and DTG diagrams of nano-SB-[PSIM]Cl at range of 25–600 C, with a temperature
increase rate of 10 °C min-1
Examining catalytic activity of nano-SB-[PSIM]Cl to promote the reaction
between arylaldehydes, b-naphthol and alkyl carbamates (Scheme 2)
After the nano-SB-[PSIM]Cl structure was identified, its catalytic activity was
examined for the production of an important class of organic compounds, i.e.,
derivatives of a-carbamatoalkyl-b-naphthols. Hence, p-nitrobenzaldehyde (1 mmol)
reacted with b-naphthol (1 mmol) and methyl carbamate (1.3 mmol) in the presence
of 0.0025–0.0125 g of the nanocatalyst at 50–75 °C in solventless conditions; the
123

Design and characterization of nano-silica-bonded…
Fig. 6 The XRD diagram of the nanocatalyst compared with the starting materials
related results are indicated in Fig. 8. As this Fig. shows, the production of the
desired a-carbamatoalkyl-b-naphthol was efficiently achieved at 70 °C using 0.01 g
of nano-SB-[PSIM]Cl (entry 4).
123

A. Zare et al.
Fig. 7 The EDX spectrum of nano-SB-[PSIM]Cl
O
OR
NH
OH
Ar
O
O
OH
Nano-SB-[PSIM]Cl
NH2 70 °C, Solvent-free
+
+
Ar
H
RO
1a-k
R = CH3, CH2Ph
Scheme 2 The synthesis of a-carbamatoalkyl-b-naphthols catalyzed by nano-SB-[PSIM]Cl
After the reaction conditions were optimized, the efficiency and generality of the
first member of heterogenized SAFIS on the production of a-carbamatoalkyl-b-
naphthols was assessed by the reaction of different aromatic aldehydes with b-
naphthol and alkyl carbamates, and the results are depicted in Table 1. As is
indicated in this Table, nano-SB-[PSIM]Cl was highly capable and general for the
production of a-carbamatoalkyl-b-naphthols. All substituents on the arylaldehydes
including nitro, methyl, methoxy, chloro, bromo, and fluoro afforded the relevant
products in short reaction times and in high yields.
In a plausible mechanism, which is illustrated in Scheme 3, we suggest that at
first, arylaldehyde is activated by the acidic group of nano-SB-[PSIM]Cl.
Afterward, b-naphthol is condensed with the activated arylaldehyde to afford
ortho-quinone methide (o-QM). Subsequently, alkyl carbamate reacts with the
123

Design and characterization of nano-silica-bonded…
Fig. 8 Optimization of the catalyst amount and temperature on the reaction of b-naphthol with p-
nitrobenzaldehyde (1 mmol) and methyl carbamate (1.3 mmol) under solvent-free conditions
activated o-QM to give a-carbamatoalkyl-b-naphthol. This mechanism is supported
by the literature [38, 40, 43, 44].
Regenerability and reusability of the nanocatalyst
The regenerability and reusability of nano-SB-[PSIM]Cl were checked by running
the reaction between p-nitrobenzaldehyde (1 mmol), b-naphthol (1 mmol) and
Table 1 The solvent-free production of a-carbamatoalkyl-b-naphthols from arylaldehydes, b-naphthol,
and alkyl carbamates using nano-SB-[PSIM]Cl at 70 °C (Scheme 2)
Ar
R
Product
Time (min)
Yielda (%)
M.p. (°C)
Found
Reported
C6H5
CH3
1a
1b
1c
1d
1e
1f
13
9
98
98
98
90
95
97
97
95
93
94b
94
221–223
202–204
248–250
241–243
189–191
201–203
195–197
173–175
178–180
181–183
187–189
(220–222) [38]
(200–202) [44]
(249–251) [38]
(241–242) [44]
(187–189) [45]
(198–200) [41]
(196–198) [41]
(172–174) [38]
(180–182) [44]
(182–184) [41]
(185–186) [41]
p-NO2C6H4
m-NO2C6H4
o-NO2C6H4
p-CH3C6H4
p-ClC6H4
m-ClC6H4
p-BrC6H4
C6H5
CH3
CH3
8
CH3
14
23
13
12
11
18
20
18
CH3
CH3
CH3
1g
1h
1i
CH3
C6H5CH2
C6H5CH2
C6H5CH2
m-CH3OC6H4
p-FC6H4
a
1j
1k
b
Isolated yield. In this reaction, 0.015 g of the catalyst was used
123

A. Zare et al.
O
S
O
HO
Ar
H
H
O
OH
O
O
O
Nanocatalyst
Nano-SB-[PSIM]Cl
Ar
Ar
H
O
S
O
O
H
O
S
HO
Ar
Ar
Ar
H
O
O
O
O
O
O
RO
NH2
Nanocatalyst
-H2O
o-QM
O
OR
NH
OH
Ar
O
+
S
O
H
O
The product
Scheme 3 The proposed mechanism for the synthesis of a-carbamatoalkyl-b-naphthols
120
100
80
60
40
20
0
Time (min)
98
Yield (%)
98
98
98
98
98
97
97
97
96
96
94
15
14
12
12
11
10
10
10
9
9
9
9
Run 1 Run 2 Run 3 Run 4 Run 5 Run 6 Run 7 Run 8 Run 9 Run 10 Run 11 Run 12
Fig. 9 The results on regenerability and reusability of nano-SB-[PSIM]Cl
methyl carbamate (1.3 mmol) for several times in the presence of 0.01 g of the
nanocatalyst at 70 °C under solventless conditions. After completion of the reaction,
the reaction mixtures were cooled to room temperature, and combined. Warm
EtOAc was added to the combined reaction mixtures, and stirred for 1 min followed
by centrifugation and decanting to separate nano-SB-[PSIM]Cl. Afterward, the
separated catalyst was washed with EtOAc, and separated from the solvent by
centrifuging and decanting. The recovered catalyst was charged by chlorosulfonic
acid according to procedure 2.2 to provide regenerated nano-SB-[PSIM]Cl. The
catalytic activity of the regenerated catalyst after 12 runs indicated no significant
loss compared with the fresh one. The results are displayed in Fig. 9.
123

Design and characterization of nano-silica-bonded…
Conclusions
In summary, we have introduced a novel, heterogeneous and attractive nanocatalyst,
namely nano-silica-bonded 3-n-propyl-1-sulfonic acid imidazolium chloride {nano-
SB-[PSIM]Cl}, for organic synthesis. In this work, we have utilized the nanocatalyst
to promote the solvent-free condensation of arylaldehydes with b-naphthol and
alkyl carbamates providing a-carbamatoalkyl-b-naphthols. The advantages of nano-
SB-[PSIM]Cl include performing the reaction in high yields and short times in the
absence of solvent under relatively mild conditions, generality, efficiency, non-
toxicity, and with a green nature.
Acknowledgments Financial support of this work by the Research Affair Office of Payame Noor
University is gratefully acknowledged.
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