Catal Lett (2015) 145:1733–1740

DOI 10.1007/s10562-015-1572-x

Preparation and Characterization of Organically Modified MCM-

48 as Heterogonous Catalyst for Oxidation of Sulfides and Thiols
Maryam Hajjami1 • Zakieh Yousofvand1

Received: 18 April 2015 / Accepted: 29 June 2015 / Published online: 9 July 2015
 Springer Science+Business Media New York 2015

Abstract MCM-48 mesoporous synthesized and grafted Keywords Zr-Schiff base-MCM-48  Mesoporous 
with aminopropyl triethoxysilane (APTES) and subse- Sulfides  Thiols
quently reacted by isatin to obtain the imine of MCM-48.
Addition of ZrOCl28H2O, leading to form the complex of
Zr(IV)/isatin-MCM-48 as new Schiff base complex of
zirconium(IV)-modified-MCM-48. The synthesized cata- 1 Introduction
lyst was characterized by XRD, TGA, FT-IR and BET. The
resulting catalyst was efficient for selective oxidation of In 1992 mesoporous material was introduced by Mobil Oil
sulfides to sulfoxides and oxidation of thiols to disulfides Company researchers. In this class MCM-41 and MCM-48
with hydrogen peroxide. In this method isolation and are outweigh. MCM-41 has a hexagonal arrangement of the
reusability of catalyst have been investigated mesopores, space group p6mm and MCM-48 has a cubic
Graphical Abstract arrangement of the mesopores, space group Ia3d. This
material that characterized by large specific surface areas
and pore sizes between 2 and 50 nm have been obtained
via the coupling of inorganic and organic components by
H2O2
template synthesis. MCM-48 is highly grace through large
specific surface area, presence of the spread network of
three- dimensional pores and pore volume. Apply modi-
H H fied-MCM-48 as catalyst has advantages like high stability
N N
O O
O under severe condition such as high temperature and
R1-S-R2 Zr R1 S R2
N N organic solvent and easy separation process [1–6]. The
O
surfaces of the MCM-48 have a large number of silanol
R-SH R-S-S-R
groups that reaction with various alkoxysilanes by covalent
EtO Si Si OEt
grafting for manufacture functionalized MCM-48 [7].
O O O O
Schiff bases are condensation products of primary amines
MCM-48 and carbonyl compounds (also known as imine or azome-
thine). Schiff bases and their metal complexes are used as
catalysts in various organic synthesis such as oxidation,
epoxidation and polymerization of alkenes. Also they are
play important role in pharmaceutical, agriculture and
industrial chemistry [8, 9]. Choosing a catalytic system for
& Maryam Hajjami oxidation of organic compounds that is heterogeneous,
mhajjami@yahoo.com; m.hajjami@ilam.ac.ir salubrious with environment and recyclable is very
1
Department of Chemistry, Faculty of Science, important [10]. Many methods have been developed for the
Ilam University, P.O. Box 69315516, Ilam, Iran heterogenization of homogeneous catalysts. But

123
1734
immobilization on silica supports offers several advantages
in terms of thermal stability, high surface areas and con-
venient porosities. That’s why todays metal-grafted func-
tionalized mesoporous silica materials used as catalyst in
many oxidation reactions. For example, Co(II) Schiff base
complex on SBA-15 was used for the oxidation of alcohols
to carbonyl compounds using molecular oxygen as oxidant
[11]. Also oxo-vanadium Schiff base complex supported
on mesoporous silica was found to be highly active and
selective for the oxidation of a variety of alcohols [12].The
Cu(II) and Ni(II) grafted mesoporous materials have been
reported as catalysts for the oxidation of olefins in the
presence of tert-butyl hydroperoxide [13]. Co(II) and
Mn(II)-amine-functionalized mesoporous SBA-15 was
produced and tested for hydroxylation of benzene using
H2O2 as oxidant in the presence of O2 atmosphere [14]. In
another report Ti-containing MCM-41 showed the highest
catalytic activity for the asymmetric oxidation of sulfide
with hydrogen peroxide in the presence of optically active
tartaric acid [15]. Also Mn(II) complex immobilized SBA-
15 was used for the asymmetric oxidation of thioanisole
[16].
Sulfoxides are important intermediates in the synthesis
of many natural and pharmalogical products [17, 18], such
as antibacterial, antifungal, anti-atherosclerotic, antihyper-
tensive [19], cardiotonic agents, psychotonics and
vasodilators [20]. Many reagents are used for the oxidation
of sulfides such as nitric acid, KMnO4, m-chloroperbenzoic
acid, sodium metaperiodate, hydrogen peroxide, sulfinyl
peroxy compounds, 4-methylmorpholine n-oxide/osmium
tetroxide, peroxotungstate complexes [21], MeNO2 solu-
tion in dilute HNO3/H2SO4 [22] and etc. In recent years, a
considerable number of methods have been reported for the
oxidation of sulfides to sulfoxides using H2O2 in combi-
nation with, V/TiO2 [23], Cerium(IV) triflate [24],
molybdate-based catalyst [25], metalloporphyrins immo-
bilized into montmorillonite [26], Zn complex [27], Cu
Salen-Fe3O4 [28], Copper(II) Schiff base complex [29],
pre-formed manganese complex [30], tantalum(V) chloride
[31] and zirconium tetrachloride [32].
The conversion of thiols to disulfides very usage both in
biological and chemical processes. For example in chem-
ical processes disulfides can be used to prepare sulfinyl and
sulfenyl compounds and in biological systems they control
the cellular redox potential and prevent oxidative damage
and formation disulfide bond is important in peptides [33–
36]. Furthermore, disulfides are relatively more stable to
organic reactions such as oxidation, alkylation and acyla-
tion compared to the corresponding free thiols, also the
thiol group can conveniently be protected as a disulfide
[37]. For the conversion of thiols to disulfides many
methods have been developed over the years to find effi-
cient these organic transformations [38–44].
123
M. Hajjami, Z. Yousofvand
However, many of these methods have drawbacks, such
as harsh acidic conditions, long reaction times, need for
expensive catalyst, unsatisfactory yields, over oxidation to
sulfones and use of not reusable catalysts. Therefore, to
improve the mentioned limitations, we decided to design a
new system for oxidation of sulfides into sulfoxides as well
as for oxidative coupling of thiols into their corresponding
disulfides using H2O2 at room temperature in the presence
of Zr complex functionalized MCM-48 as mesoporous
catalyst.
2 Experimental
2.1 Materials and Instrumentation
All reagents and used materials were buying from Sigma-
Aldrich and Merck, and were used any additional purifi-
cation. All the melting points were recorded by open
capillary method and are uncorrected. IR spectra were
recorded in KBr on a BOMEN Infra-Red Spectropho-
tometer FT-IR. Thermogravimetric analysis (TGA) was
used with a heating rate of 10 C/min in air and the sam-
ples were heated from room temperature to 850 C. X-ray
diffraction (XRD) patterns were recorded using a Cu Ka
radiation source with wave length 1.54 Å. N2 adsorption/
desorption measurements analysis (BET) were recorded by
BEL sorp-mini II (volumetric adsorption analyzer, Japan).
All of the samples were degassed at 100 C for 5 h before
analysis and range of relative pressures (p/po) was
0.028–0.989. The specific surface area of the synthesized
materials was evaluated using the BET method, and the
pore size distribution was calculated by the BJH method.
2.2 Synthesis of MCM-48 at Room Temperature
(Sol Gel)
2.6 g of CTAB was added to 120 mL of deionized H2O
and 50 mL of ethanol under stirring. When CTAB was
completely dissolved, 12 mL of NH4OH were added. After
that, 3.6 mL of TEOS was poured into the solution
immediately under vigorous stirring during 16 h at room
temperature. The solid product was recovered by filtration
and dried at room temperature overnight. The CTAB was
removed from the in organic material by calcination of the
sample at 540 C for 9 h [45].
2.3 Synthesis of Zirconium(IV) Modified-MCM-48
For grafting of MCM-48 by 3-aminopropyltriethoxysilane,
first 4.8 g 3-aminopropyltriethoxysilane added to 4.8 g of
MCM-48 in 96 mL n-hexane and the reaction mixture was
stirred under reflux condition for 24 h at nitrogen
Preparation and Characterization of Organically Modified MCM-48 as Heterogonous Catalyst…
atmosphere. Then the resulting white solid was filtered,
washed with n-hexane and dried at room temperature for
24 h to obtain aminofunctionalized MCM-48 (MCM-48-
nPr-NH2) [46]. Then isatin and MCM-48-nPr-NH2 with
ratio 2:1 were added to absolute ethanol and 0.5 mL of
acetic acide and refluxed for 3 h. Then the mixture was
filtered washed with ethanol and dried at room temperature,
resulting is a yellow sediment. Finally ZrOCl28H2O was
added to this sediment (with ratio 2:1) in acetonytrile and
mixture was stirred for 6 h at room temperature. Then the
resulting product was washed with water to remove excess
of Zirconium(IV) (Sheme 1).
2.4 General Procedure for the Oxidation of sulfides
to sulfoxide
A mixture of sulfide (1 mmol), H2O2 (0.4 mL) and catalyst
(0.01 g) at room temperature, was stirred under solvent-
free condition for the certain period of time. The reaction
was monitored by thin-layer chromatography (TLC). Upon
completion, the reaction mixture was decanted and
extracted with dicoloromethan. The organic layer was dried
over anhydrous Na2SO4 (1.5 g). Finally, the organic sol-
vents were evaporated, and products were obtained in
82–99 % yield.
2.5 General Procedure for the Oxidation of Thiols
to Disulfides
A mixture of thiol (1 mmol), H2O2 (0.4 mL) and catalyst
(0.01 g) was stirred in ethanol at room temperature for the
certain period of time. The reaction was monitored by
TLC. After completion of the reaction, the catalyst was
separated by simple filtration and the mixture was washed
with CH2Cl2 (5 9 2 mL), and next, the product was
extracted with CH2Cl2 (5 mL 9 4). The organic layer was
dried over anhydrous Na2SO4 (1.5 g). After the evapora-
tion of dicoloromethan gave the pure products in 85–98 %
yields.
O OEt
MCM-48
(EtO)3Si(CH2)3NH2 Si
MCM-48
O Si-MCM-48 is retained for the catalyst after one used.
n-Hexane, reflux O
24 h, N2 Si
O
OEt
NH
O OEt
MCM-48
N
MCM-48
Si ZrOCl2.8H2O
O O
O O
O CH3CN, rt
Si N Si
O
OEt
NH
6h
Scheme 1 Zirconium(IV)-modified-MCM-48 synthesis
1735
3 Result and Discussion
3.1 Catalyst Synthesis and Characterization
In this work the Zirconium(IV)-modified-MCM-48 were
synthesis using Zirconium(IV) oxide chloride octahydrate
and the Schiff base supported MCM-48 in CH3CN. The
Zirconium(IV)-modified-MCM-48 were then characterized
using a variety of different techniques. The TGA curves of
the MCM-48, MCM-48- nPr-NH2, MCM-48-nPr-N-isa-
tin(Schiff base) and MCM-48-nPr-N-isatin- Zirconium
(Schiff base Complex) show the mass loss of organic
material as they decompose upon heating (Fig. 1). The
initial weight loss from the MCM-48 (\100 C) is due to
the removal of physically adsorbed water and surface
hydroxyl group. The weight loss of about 2.55 %. The
weight loss (4.75 %) between 100 and 840 C is attributed
mainly to the condensation of silanol groups and removal
of chemically adsorbed water. MCM-48-nPr-NH2 shows
four-step weight loss behavior. Weight loss of MCM-48-
nPr-NH2 appears about 10.32 % at 107–572 C, which is
contributed to the thermal decomposition of the 3-amino-
propyl trietoxysilan groups (equivalent 0.466 mmol). For
MCM-48- nPr-N-isatin(Schiff base), the weight loss of
19.05 % between 115 and 684 C that related to the
breakdown of the isatin (equivalent 0.59 mmol). For
MCM-48-nPr-N-isatin-Zirconium (Schiff base Complex)
the weight loss about 16.03 % between 102 and 657 C
that is due to decompose of ZrOCl2 (equivalent
0.17 mmol). On the basis of these results, the well grafting
of aminopropyltriethoxysilane, isatin and Zirconium (IV)
groups on the MCM-48 is verified.
Figure 2 shows XRD patterns for MCM-48, MCM-48-
nPr-NH2, MCM-48-nPr-N-isatin, MCM-48-nPr-N-isatin-
Zirconium and used Catalyst. XRD patterns illustrate typ-
ical peaks corresponding to diffraction at (211), (220), (420)
and (332) that can be indexed to Ia3d cubic structure. Some
loss in the intensities of the peaks was observed upon
modification with 3-aminopropyltriethoxysilane, isatin and
Zirconium which shows that though there is some reduction
in the crystallinity of Si-MCM-48. Also the mesoporosity of
NH2 Isatin, EtOH, AcOH
NH2 Reflux, N2, 3h These results provide further evidence that functionaliza-
tion occurring mainly inside the mesopore channels.
Additionally, the unit parameter cell (the center-to-cen-
NH
O OEt ter pore distance) (a0) of 82.1 Å was calculated by using
Si N
O O d211-spacing values according with the following Eq. [25].
O Zr
O
N
O
OEt a0 ¼ d211 ð6Þ1=2 ð1Þ
NH
Figure 3 shows the FT-IR spectra of the MCM-48,
MCM-48-nPr-NH2, MCM-48-nPr-N-isatin, MCM-48-nPr-
N-isatin-Zirconium that exhibited a significant difference
123
1736 M. Hajjami, Z. Yousofvand

Fig. 1 TGA curve of the

MCM-48, MCM-48-nPr-NH2,
MCM-48-nPr-N-isatin and
MCM-48-nPr-N-isatin-
Zirconium (Catalyst)

2500
211
MCM-48
Amine-MCM-48
2000 Imine-MCM-48
Zr-Imine-MCM-48
Zr-Imine-MCM-48- After use
Intensity, (a.u)

1500

1000 220

500 420
332

0
2 4 6 8
Diffraction angle, 2 theta

Fig. 2 XRD patterns of the MCM-48, Amine-MCM-48, Imine-

MCM-48, Zr-imine-MCM-48 and used Catalyst

as a compared. In the all spectra, the peaks at 3445 and

756 cm-1, which are assigned to O–H and Si–O stretching
of the surface silanols of the MCM-48, the sharp peak at
1080 cm-1 can be attributed to the asymmetric stretching
vibration of the Si–O–Si band and 800 cm-1 can be
assigned to the symmetric stretching vibration of Si–O. In
the spectra of MCM-48-nPr-NH2, the peak at 1524 and Fig. 3 FT-IR spectra of the a MCM-48, b MCM-48-nPr-NH2,
1638 cm-1 can be assigned to the amine functionality (N– c MCM-48-nPr-N-isatin, d MCM-48-nPr-N-isatin-Zirconium
H bending vibration). In the spectra of MCM-48-nPr-N-
isatin (Schiff base), a certain band in the 1624 cm-1 that
due to C=N in the Schiff base. Also in the spectra of cat- IV according to IUPAC nomenclature with H1 hysteresis
alyst observed this same peak shift to 1634.29 cm-1. loops which are representing mesoporous for the expanded
Based on inductively coupled plasma atomic emission materials. Also, steep condensation step in the relative
spectroscopy (ICP-AES), the amounts of Zr(IV) in the pressure range of 0.1–0.3 observed which is associated
complex Schiff-base-MCM-48 was 0.695 mmol/g. with capillary condensation in the channels of MCM-48
The nitrogen adsorption–desorption isotherms of MCM- and indicating a good structural order. These results are in
48 silicas is presented in Fig. 4. The obtained results agreement with those previously reported in the literature
showed nitrogen adsorption–desorption isotherms of type [47, 48].

123
Preparation and Characterization of Organically Modified MCM-48 as Heterogonous Catalyst… 1737

Physicochemical and structural parameters of the 3.2 Catalytic Studies

samples obtained by N2 isotherms are summarized in
Table 1. MCM-48 showed high surface areas and pore
volume, which is typical of mesoporous materials; nev-
ertheless, decrease in the SBET and DBJH average pore
diameter was observed with functionalization in Amine-
MCM-48, Schiff base-MCM-48 and Zr-Schiff base-
MCM-48. This result can be easily interpreted due to the
fact that the presence of pendant group on the surface that
partially blocks the adsorption of nitrogen molecules.
Such significant decrease of textural properties of porous
materials on grafting was already reported [49].The wall
The prepared catalyst was assessed for its activity in the
oxidation of sulfides and thiols (both aliphatic and aro-
matic) to form sulfoxides and disulfides as the principal
products (Scheme 2). Thus, after screening different
amounts of the synthesized catalyst (Table 2), the results
1.2
1.0

thickness of MCM-48 was 14.3 Å where calculated by the

0.8
following equation [50]:
MCM-48

 

dvp /drp
Amine-MCM-48
Wall thickness ¼ a0=3:092  DBJH=2 ð2Þ 0.6
Imine-MCM-48
Zr-Imine-MCM-48
0.4
Pore size distribution (ADS) of MCM-48 according to
BJH methods is presented in Fig. 5. After functionaliza- 0.2
tion, a decrease in the DBJH and SBET average pore
diameter was observed that can be easily interpreted due 0.0
to the fact that the presence of pendant group on the
2 4 6 8 10 12 14
surface that partially blocks the adsorption of nitrogen
rp , nm
molecules.
Fig. 5 Pore size distribution (ADS) of synthesized materials

600
Volume adsorbed, cm -3/g STP

adsorption (MCM-48)
desorption
adsorption (Amine-MCM-48)
desorption
400 adsorption (Imine-MCM-48)
desorption
adsorption (Zr-Imine-MCM-48)
desorption

200
Scheme 2 Oxidation of sulfides to sulfoxide and coupling of thiols to
disulfides

0.0 0.2 0.4 0.6 0.8 1.0

Relative pressure, (p/p0 ) Table 2 Results of varying the amount of catalyst
Entry Amount of catalyst (g) Time (min) Yield (%)a
Fig. 4 Nitrogen adsorption–desorption isotherms of synthesized
materials 1 0.005 40 25b
2 0.008 40 76b
3 0.01 40 99
4 0.025 40 94
Table 1 Textural properties of synthesized materials obtained by 5 0.006 180 55b
nitrogen adsorption–desorption analysis
6 0.01 10 96
Sample name SBET (m2 g-1) DBJH (nm) VTotal (cm3 g-1) 7 0.02 25 90

MCM-48 1326 2.44 1.12 Reaction conditions dibenzilsulfide (1 mmol), H2O2 (0.4 mL), sol-
Amine-MCM-48 554 1.70 0.40 vent-free and room temperature (Entry 1–4), 2-naphthalene thiol
(1 mmol), H2O2 (0.4 mL), ethanol and room temperature
Imine- MCM-48 369 1.67 0.41 a
Isolated yields
Zr-Imine- MCM-48 248 1.21 0.21 b
Purification by preparative TLC

123
1738 M. Hajjami, Z. Yousofvand

Table 3 Oxidation of sulfides and coupling of thiols with H2O2 in the presence of Zr(IV)/isatin-MCM-48 at room temperature
Entry Substrate Product Time (min) Yield (%)a TON (9104) M.p (C)

1 30 99 15.66 123–125/128–132 [28]

2 30 82 12.97 Oil/oil [28]

3 35 97 15.35 118–122/116–121 [28]

4 10 90 14.24 Oil/oil [28]

5 15 96 15.19 84–86/87–89 [28]

6 90 82 12.97 Oil/oil [28]

7 65 90 14.24 111–113/110–114 [51]

8 5 82 12.97 Oil/oil [28]

9 10 96 15.19 129–133/134–136 [28]

10 10 98 15.51 169–173/174–175 [28]

11 60 98 15.51 87–91/94–96 [28]

12 5 85 13.45 36–38/38–40 [28]

13 10 90 14.24 Oil/oil [28]

14 15 98 15.51 101–104/103 [28]
a
Reaction conditions: sulfide or thiol (1 mmol), catalyst (0.01 g) and H2O2 (0.4 mL)
b
Isolated yields

show that 0.01 g of catalyst was the best amounts for both
oxidation reaction.
According to the obtained results, the optimized reaction
conditions were selected to determine the scope of func-
tionalized MCM-48 catalyzed the oxidation reactions. In
this light a wide range of aliphatic and aromatic sulfides
and thiols were subjected to oxidize to corresponding sul-
foxides and disulfides in the presence of 0.01 g modified
MCM-48 catalyst. The turn over numbers were calculated
and results are summarized in Table 3. It should be noted,
in this optimized reaction conditions, selective oxidation of
sulfides to sulfoxides have been observed without any over-
oxidation to sulfones. Interestingly, either upon the use of
an excess amount of H2O2 or much more time stirring the
reaction mixture, the formation of sulfone as by product
did not observed.
A plausible oxidation reaction mechanism is shown in
Scheme 3 [52]. The role of Zr (IV) in modified MCM-48 as

123
Preparation and Characterization of Organically Modified MCM-48 as Heterogonous Catalyst…
Scheme 3 Proposed
mechanism for the oxidation of
sulfides
Fig. 6 The recycling experiment of catalyst for oxidation of dibenzyl
sulfide to dibenzyl sulfoxide at room temperature under solvent-free
condition after 30 min
catalyst is to form the active oxidant–sulfide complex.
Finally, transfer of oxygen to sulfur leads to the formation
of sulfoxide.
3.3 Reusability and Recycling of the Catalyst
The catalyst can be efficiently recovered after reaction by
simple filtration. The separated catalyst was reused for
many times. Reusability and recycling of the catalyst was
examined through a series of sequential condensations of
the oxidation of dibenzyl sulfide to dibenzylsulfoxide at
room temperature as a model reaction. In a typical reaction,
the catalyst was recovered by simple filtration from the
reaction mixture and reused for five cycles without any
significant loss of its activity (Fig. 6). The nature of the
1739
recovered catalyst after one used was investigated by XRD
at Fig. 2.
4 Conclusion
In summary, zirconium-modified-MCM-48 was prepared
and found as an efficient heterogeneous catalyst for oxi-
dation of sulfides to sulfoxides and thiols to disulfides. This
method has many privilege including, high product in
present of small amount of catalyst, excellent isolated and
simple work-up, stand heterogeneous, short reaction time
and accordance with green chemistry principal.
Acknowledgments The authors acknowledge Ilam University,
Ilam, Iran for financial support of this work.
References
1. Polarz S, Smarsly B (2002) J Nanosci Nanotechnol 2:581–612
2. Guan LC, Nur H, Endud S (2006) J Phys Sci 17:65–75
3. Schumacher K, Ravikovitch PI, Chesne AD, Neimark AV, Unger
KK (2000) Langmuir 16:4648–4654
4. Banerjee S, Balasanthiran V, Koodali RT, Sereda GA (2010) Org
Biomol Chem 8:4316–4321
5. Hoffmann F, Cornelius M, Morell J, Froba M (2006) Angew
Chem Int Edit 45:3216–3251
6. Jun S, Kim JM, Ryoo R, Ahn YS, Han MH (2000) Microporous
Mesoporous Mater 41:119–127
7. Ojani R, Raoof JB, Fathi S (2009) J Solid State Electron
13:837–842
8. Kumar S, Dhar DN, Saxena PN (2009) J Sci Ind Res India
68:181–187
9. Khandar AA, Hosseini-Yazdi SA, Zarei SA (2005) Inorg Chim
Acta 358:3211–3217
123
1740
10. Rahmani N, Khalili R, Rahimi M (2013) Rabbani. Monatsh
Chem 144:597–603
11. Rana BS, Jain SL, Singh B, Bhaumik A, Sain B, Sinha AK (2010)
Dalton Trans 39:7760–7767
12. Verma S, Nandi M, Modak A, Jain SL, Bhaumik A (2011) Adv
Synth Catal 353:1897–1902
13. Nandi M, Roy P, Uyama H, Bhaumik A (2011) Dalton Trans
40:12510–12518
14. Kalbasi RJ, Massah AR, Zamani F, Bain AD, Berno B (2011) J
Porous Mater 18:475–482
15. Iwamoto M, Tanaka T, Hirosumi J, Kita N, Triwahyono S (2001)
Microporous Mesoporous Mater 48:271–277
16. Alavi S, Hosseini-Monfared H, Aleshkevych P (2014) RSC Adv
4:48827–48835
17. Rahimizadeh M, Rajabzadeh G, Khtami SM, Eshghi H, Shiri A
(2010) J Mol Catal A 323:59–64
18. Koposov AY, Zhdankin VV (2005) Synthesis 1:22–24
19. Shaabani A, Rezayan AH (2007) Catal Commun 8:1112–1116
20. Golchoubian H, Hosseinpoor F (2007) Molecules 12:304–311
21. Ghaemi A, Rayati S, Zakavi S, Safari N (2009) Appl Catal A
353:154–159
22. Liu P, Liu SJ, Zhang JZ, Tian GR (2005) Synth Commun
35:3173–3177
23. Negi SS, Sivaranjani K, Singh AP, Gopinath CS (2013) Appl
Catal A 452:132–138
24. Raju BR, Sarkar S, Reddy UC, Saikia AK (2009) J Mol Catal A
308:169–173
25. Bayat A, Shakourian-Fard M, Hashemi MM (2014) Catal Com-
mun 52:16–21
26. Zhou X-T, Ji H-B (2014) Catal Commun 53:29–32
27. Wu X-F (2012) Tetrahedron Lett 53:4328–4331
28. Ghorbani-Choghamarani A, Ghasemi B, Safari Z, Azadi G (2015)
Catal Commun 60:70–75
29. Gogoi P, Kalita M, Bhattacharjee T, Barman P (2014) Tetrahe-
dron Lett 55:1028–1030
30. Dai W, Li G, Wang L, Chen B, Shang S, Lv Y, Gao S (2014)
RSC Adv 4:46545–46554
31. Kiriharaa M, Yamamoto J, Noguchi T, Hirai Y (2009) Tetrahe-
dron Lett 50:1180–1183
123
M. Hajjami, Z. Yousofvand
32. Bahrami K (2006) Tetrahedron Lett 47:2009–2012
33. Ruano JLG, Parra A, Aleman J (2008) J Alem Green Chem
10:706–711
34. Silveira CC, Mendes SR (2007) Tetrahedron Lett 48:7469–7471
35. Montazerozohori M, Karami B, Azizi M (2007) Arkivok
1:99–104
36. Hosseinzadeh R, Tajbakhsh M, Khaledi H, Ghodrati K (2007)
Monatsh Chem 138:871–873
37. Thurow S, Pereira VA, Martinez DM, Alves D, Perin G, Jacob
RG, Lenardão EJ (2011) Tetrahedron Lett 52:640–643
38. Feng J, Lv M-F, Lu G-P, Cai C (2015) Org Biomol Chem
13:677–681
39. Ghorbani-Choghamarani A, Azadi G, Tahmasbi B, Hadizadeh-
Hafshejani M, Abdi Z (2014) Phosphorus Sulfur 189:433–439
40. Nikoorazm M, Ghorbani-Choghamarani A, Ghorbani F, Mahdavi
H, Karamshahi Z (2015) J Porous Mater 22:261–267
41. Abdel-Mohsen HT, Sudheendran K, Conrad J, Beifuss U (2013)
Green Chem 15:1490–1495
42. Yan J, Tao H, Zeng M, Tao J, Zhang S, Yan Z, Wang W, Wang J
(2009) Chin J Catal 30:856–858
43. Saxena A, Kumar A, Mozumdar S (2007) J Mol Catal A
269:34–40
44. Joshi AV, Bhusare S, Baidossi M, Qafisheh N, Sasson Y (2005)
Tetrahedron Lett 46:3583–3585
45. Meléndez-Ortizn HI, Perera-Mercado YA, Garcı́a-Cerda LA,
Mercado-Silva JA, Castruita G (2013) Ceram Int 404:155–4161
46. Chen H, Wang Y (2002) Ceram Int 28:541–547
47. Meléndez-Ortiz HI, Perera-Mercado Y, Mercado-Silva JA, Oli-
vares-Maldonado Y, Griselda G, Garcı́a-Cerda LA (2014) Ceram
Int 40:9701–9707
48. Lee JW, Cho DL, Shim WG, Moon H (2004) Korean J Chem Eng
21:246–251
49. Hajjami M, Ghorbani F, Bakhti F (2014) Appl Catal A
470:303–310
50. Wang K, Lin Y, Morris MA, Holmes JD (2006) J Mater Chem
16:4051–4057
51. Yang C, Jin Q, Zhang H, Liao J, Zhu J, Yu B, Deng J (2009)
Green Chem 11:1401–1405
52. Das R, Chakraborty D (2010) Tetrahedron Lett 51:6255–6258