ZnFe2O4 nanoparticles: A green and recyclable magnetic catalyst for fast and regioselective conversion of epoxides to vicinal hydroxythiocyanates using NH4SCN under solvent-free conditions

Article abstract of DOI:10.1080/10426507.2017.1390460

ZnFe₂O₄ nanoparticles were synthesized and used as recyclable magnetic catalyst in the solvent-free conversion of different epoxides to vicinal hydroxythiocyanates with NH₄SCN at room temperature. The reactions were carrie

Full text of DOI:10.1080/10426507.2017.1390460

Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: http://www.tandfonline.com/loi/gpss20
ZnFe2O4 nanoparticles: A green and
recyclable magnetic catalyst for fast and
regioselective conversion of epoxides to vicinal
hydroxythiocyanates using NH4SCN under solvent-
free conditions
Ronak Eisavi & Somayieh Alifam
To cite this article: Ronak Eisavi & Somayieh Alifam (2017): ZnFe2O4 nanoparticles: A green
and recyclable magnetic catalyst for fast and regioselective conversion of epoxides to vicinal
hydroxythiocyanates using NH4SCN under solvent-free conditions, Phosphorus, Sulfur, and Silicon
and the Related Elements, DOI: 10.1080/10426507.2017.1390460
To link to this article: http://dx.doi.org/10.1080/10426507.2017.1390460
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ZnFe2O4 nanoparticles: A green and recyclable magnetic catalyst for fast and regioselective
conversion of epoxides to vicinal hydroxythiocyanates using NH4SCN under solvent-free
conditions
Ronak Eisavi,* Somayieh Alifam
Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran
E-mail: roonak.isavi@gmail.com
Abstract
ZnFe2O4 nanoparticles were synthesized and used as recyclable magnetic catalyst in the solvent-
free conversion of different epoxides to vicinal hydroxythiocyanates with NH4SCN at room
temperature. The reactions were carried out by grinding in a mortar with perfect regioselectivity
within short times (2-25 min) and with high to excellent yields (75-95%). The nanocatalyst was
separated easily using an external magnet and reused for four consecutive cycles without any
noticeable loss of efficiency or magnetic property.
Graphical Abstract
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Keywords: epoxide, nano ZnFe2O4, NH4SCN, solvent-free, vicinal hydroxythiocyanate
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1. Introduction
Nowadays, removal of toxic and volatile solvents from chemical reactions in order to realize the
aims of green chemistry is one of the main challenges facing organic chemists. Using solvent-
free conditions is one of the best ways to achieve this goal.1 The use of grinding technique under
solvent-free conditions has unique advantages such as low cost, simplified workups, eliminating
of pollution, reduced explosion risk, and benign conditions.2 In recent years, although magnetic
nano-ferrites due to biological utilizations such as drug delivery properties have received
remarkable attention,3 their catalytic potentials have not been much considered in organic
transformations.4,5 Recently, magnetic nanocatalysts have been successfully used for
accomplishing several organic reactions.6-10 Among these nanoparticles, ZnFe2O4 is an effective
heterogeneous nanocatalyst. It has a high surface area and amazing properties such as
economical price, recoverability, eco-friendliness and effortless separation that shows perfect
regioselectivity to generate high yields of products within short reaction times under mild
circumstances.11-13
Thiocyanates are valuable intermediates that play a key role in biochemistry, agriculture and
pharmaceuticals.14-16 Preparation of thiiranes from epoxides with thiocyanate ions is carried out
through intermediacy of the corresponding vicinal hydroxythiocyanates, but these compounds
are not isolated due to quick conversion to thiiranes.17 Hence, the synthesis of these precious
intermediates is of paramount importance. Although few methods for the synthesis of vicinal
hydroxythiocyanates bearing aryl or alkyl groups have been reported in the literature, some of
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them suffer from limitations such as expensive and non-recyclable catalysts, the use of toxic
solvents, difficult and tedious workup procedures, low regioselectivity and product yields, long
reaction times and harsh reaction conditions.18-31 Therefore, inspired by the remarkable effects of
zinc nano-ferrites, and in connection with our works on nanoparticles32,33 and synthesis of 1,2-
difunctional derivatives from epoxides,34-38 herein, we want to introduce nano ZnFe2O4 as a
green recyclable catalyst for the rapid and regioselective conversion of different epoxides to aryl
or alkyl substituted vicinal hydroxythiocyanates through attack of thiocyanate ions to the α- or β-
position respectively, under solvent-free conditions at room temperature (Scheme 1).
R
R
R
NH4SCN/Nano ZnFe2O4
solvent-free, r.t., grinding
OH
SCN
or
O
SCN
OH
-attacked
-attacked
R = aryl, alkyl, allyl
Scheme 1. Preparation of vicinal hydroxythiocyanates bearing different groups in the presence
of catalytic amounts of nano ZnFe2O4.
2. Results and Discussion
2.1. Characterization of the catalyst
The synthesized ZnFe2O4 nanoparticles39 were characterized by X-ray diffraction (XRD),
scanning electron micrograph (SEM) and FT-IR techniques. Figure 1 shows an XRD pattern of
the ZnFe2O4 nanoparticles. The X-ray pattern displays sharp peaks coinciding with the standard
data of the spinel ZnFe2O4 (Franklinite) phase (JCPDS card No. 74-2397). The average
crystallite size of these nanoparticles was calculated to be about 43 nm using Scherrer’s
equation.40 The morphology of the synthesized nanocatalyst was confirmed by scanning electron
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microscopy (Figure 2). The SEM image shows that the size of spherical zinc ferrite nanoparticles
is between 43 to 46 nm. These results are in perfect harmony with the XRD data. Figure 3
represents the FT-IR spectrum of the nano ZnFe2O4. A broad band at 3421 cm1 is due to
stretching mode of H2O molecules indicating the presence of OH groups on the surface of
nanoparticles. The band at 1637 cm−1 corresponds to the bending mode of H2O molecules. The
absorption bands in the range of 1000-400 cm1 are assigned to metal-oxygen stretching
vibrations of the ferrite spinel structure. A strong band at 548 cm1 is related to the Fe-O
stretching vibration at the tetrahedral site.41 Magnetic characterization of ZnFe2O4 nanoparticles
was carried out using a Vibration Sample Magnetometer (VSM) at room temperature (Figure 4).
The variation of magnetization as a function of applied field shows a narrow cycle, and the
hysteresis loop of the sample presents the behavior of soft ferromagnetic materials.
Figure 1. The X-ray diffraction pattern of calcinated nano ZnFe2O4
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Figure 2. The SEM images of nano ZnFe2O4
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Figure 3. FT-IR (KBr) spectrum of nano ZnFe2O4
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Figure 4. Magnetic hysteresis loop of nano ZnFe2O4 at room temperature
2.2. Conversion of epoxides to vicinal hydroxythiocyanates with NH4SCN catalyzed by nano
ZnFe2O4
Table 1 shows optimization experiments for the reaction of styrene oxide, NH4SCN and ZnFe2O4
nanoparticles under different conditions. The best result in terms of molar ratio, selectivity,
reaction time and mild conditions was obtained using 1 mmol styrene oxide, 1 mmol NH4SCN
and 5 mol% of nano ZnFe2O4 at room temperature by grinding in the mortar under solvent-free
conditions. The method was regioselective. Thiocyanate attack at the phenyl substituted carbon
(α-position) led to 2-hydroxy-1-phenylethyl thiocyanate as the only product in excellent yield
(Table 1, entry 3). In order to optimize the quantity of catalyst, the reaction was carried out using
different amounts of nano ZnFe2O4 (3, 5 and 10 mol%). It is noteworthy that in the absence of
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catalyst, the reaction was not accomplished. To evaluate the effect of solvent, the reaction was
performed in the presence of various solvents such as acetonitrile, chloroform, n-hexane, ethanol
and ethyl acetate. The results showed that the phenyl substituted vicinal hydroxythiocyanate
could not be obtained in the presence of solvent and the only generated product was styrene
episulfide in acetonitrile after 15 min. The reaction did not occur in the presence of chloroform
and n-hexane after 50 min. By the use of ethanol and ethyl acetate, the reaction was not complete
and led to the production of thiirane.
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Table 1. Nano ZnFe2O4 catalyzed reaction of styrene oxide with NH4SCN under different
conditionsa
Nano ZnFe2O4
Ph
S
Ph
+
NH4SCN
or
OH
O
Ph
SCN
Nano
Entry ZnFe2O4
(mol%)
β-Hydroxy-
NH4SCN
Time
(min)
Thiirane Epoxideb
Conditions
thiocyanate
(mmol)
(%)
0
(%)
100
(%)
0
1
2
3
4
5
6
-
2
Solvent-
free/r.t./grinding
Solvent-
40
20
10
10
8
3
1
1
2
1
2
80
0
0
0
0
0
20
0
free/r.t./grinding
Solvent-free/r.t.
/grinding
5
100
100
100
100
5
Solvent-free/r.t.
/grinding
0
10
10
Solvent-free/r.t.
/grinding
0
Solvent-free/r.t.
/grinding
8
0
7
8
5
5
5
5
5
1
1
1
1
1
CH3CN/r.t.
15
50
50
40
45
0
0
100
0
0
CHCl3 / r.t.
100
100
50
9
n-Hexane / r.t.
C2H5OH/r.t.
Ethyl Acetate/r.t.
0
0
10
50
0
11
30
0
70
a All reactions were carried out with 1 mmol of styrene oxide. b Yield of recovered styrene oxide.
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The capability and generality of this procedure was further studied by solvent-free reactions of
various epoxides carrying electron-withdrawing and -donating groups under the optimum
conditions. All epoxides were simply converted to aryl or alkyl substituted vicinal
hydroxythiocyanates in high yields and with perfect regioselectivity. A notable advantage of this
synthetic method is that the formation of thiirane as a side-product was not observed and vicinal
hydroxythiocyanates were produced as the only products in all reactions (Table 2).
Table 2. Conversion of epoxides to vicinal hydroxythiocyanates bearing different groups with
a
NH4SCN in the presence of nano ZnFe2O4
vicinal hydroxythiocyanate
(b)
Yield
(%)b
Entry
1
Epoxide (a)
Time (min)
10
Ref.
90
89
42,43
OH
O
SCN
Cl
Cl
Br
2
12
23
OH
O
SCN
Br
3
4
5
12
15
25
89
90
90
23
26
OH
O
O
SCN
SCN
OH
42,43
SCN
O
O
O
OH
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6
7
25
7
91
90
18
SCN
O
O
O
OH
42,43
O
SCN
O
O
OH
O
SCN
O
8
9
10
7
92
91
75
42,43
43
O
OH
O
SCN
O
O
OH
SCN
Cl
Cl
10
2
42
O
OH
O
O
11
4
90
43
O
SCN
O
O
OH
SCN
12
13
9
3
89
90
23,42
22
O
OH
SCN
O
OH
OH
SCN
O
14
4
95
42,43
a All reactions were carried out with 1 mmol of epoxide in the presence of ammonium
thiocyanate (1mmol) under solvent-free conditions at room temperature. b Yields refer to isolated
pure products.
Although the exact mechanism of this reaction is still unclear the following pathways seems
however reasonable (Scheme 2). As shown in Scheme 2, the regioselectivity of the ring opening
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of epoxides depends on the reaction mechanism, and it is especially influenced by steric and
electronic factors. For epoxides bearing alkyl groups, the steric factor is prevailing and the
nucleophilic attack of thiocyanate anion at the less hindered carbon atom of epoxides is
significantly preferred (SN2 type mechanism). On the opposite side, for epoxides bearing aryl
groups, the electronic factor is dominant and the nucleophilic attack of the thiocyanate anion is
favored at the more stabilized benzylic carbocation (SN1 type mechanism).
_
R
R
R
SCN
OH
SCN
(a): SN1
(b): SN2
+
+
R
R
O
+
O
O
R
O
OH
_
+
(b)
(a): R = aryl
SCN
(b): R = alkyl, allyl
SCN
SCN
: Nano ZnFe2O4
Scheme 2. A proposed mechanism for the conversion of epoxides to vicinal hydroxythiocyanates
bearing different groups with the NH4SCN/nano ZnFe2O4 system.
Performing the reaction under solvent-free conditions, recyclability and reusability of the
ZnFe2O4 nanoparticles are the green aspects of this methodology. After completion of the
reaction, the nano-ferrite particles are conveniently collected by an external magnet, washed with
double distilled water three times, dried at 80°C for 2 h and applied for the next run. The
nanocatalyst can be reused four times without loss of magnetic property or catalytic activity
(Figure 5).
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90%
90%
89%
89%
88%
88%
87%
cycle 1
cycle 2
cycle 3
cycle 4
cycle 5
Figure 5. Recycling of nano ZnFe2O4 in the conversion of styrene oxide to 2-hydroxy-1-
phenylethyl thiocyanate.
The advantages of the present synthetic method were revealed by comparison of conversion of
styrene oxide to 2-hydroxy-1-phenylethyl thiocyanate with the methods reported in the literature
(Table 3). In viewpoints of recoverability, easy preparation and separation of magnetic
nanocatalyst, perfect regioselectivity, short reaction times, mild and eco-friendly conditions and
high efficiency, our procedure is more preferable.
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Table 3. Comparison of the reaction of styrene oxide with NH4SCN in the presence of various
catalysts a.
Catalyst
Ph
Ph
Ph
+
NH4SCN
+
OH
SCN
O
SCN
(I)
OH
(II)
NH4SCN
Time
(min)
Yield
Entry
Catalyst
Conditions
Product
Ref.
b
(mmol)
(%)
Nano ZnFe2O4 (5
mol%)
solvent-free/ r.t./
grinding
1
2
3
1
I
10
50
15
90
Selectfluor (10
mol%)
95
(16:84)
88
1
2
CH3CN/r.t.
H2O/reflux
I+II
18
31
MPTC (20 mol%)
DDQ (10 mol%)
I+II
(5:95)
91
4
5
6
3
1.5
3
CH3CN/reflux
H2O/r.t.
50
18
60
14
23
27
I+II
I
(89:11)
92
GaCl3 (10 mol%)
PEG-SO3H (10
mol%)
84
H2O/r.t.
I+II
(5:95)
83
PEG-SO3H (10
mol%)
7
8
3
1
1
3
3
CH2Cl2/r.t.
60
20
45
90
25
25
20
26
21
30
I+II
I+II
I+II
I+II
I+II
(96:4)
T(4-OHP)P (10
mol%)
CH3CN/reflux
CH3CN/reflux
CH3CN/reflux
CH3CN/82 °C
96
95
(17:83)
90
9
PPI (20 mol%)
PTC (0.1 g)
10
11
(90:10)
94
TABCO (150
mol%)
(93:7)
a All reactions were carried out with 1 mmol of styrene oxide. bThe present method.
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3. Conclusion
In summary, we have demonstrated that nano ZnFe2O4 is an efficient catalyst for the conversion
of different epoxides to the corresponding aryl and alkyl substituted vicinal hydroxythiocyanates
at room temperature under solvent-free conditions. This novel method exhibits several
remarkable advantages including perfect regioselectivity, short reaction times, high yields, eco-
friendly and benign conditions, simple work-up, and the use of recyclable and reusable magnetic
nanocatalysts which recommend the described protocol as a preferable method for the
preparation of vicinal hydroxythiocyanates bearing aryl and alkyl groups from epoxides.
4. Experimental
4.1. General
All reagents and substrates were purchased from commercial sources with the best quality and
they were used without further purification. The synthesized nano ZnFe2O4 was characterized by
XRD on a Bruker D8-Advanced diffractometer with graphite-monochromatized Cu Kα radiation
(λ = 1.54056 Å) at room temperature. SEM images were determined on a LEO 1430 VP
scanning electron microscopy. The magnetic property of the nano ZnFe2O4 was measured using
a VSM (Meghnatis Daghigh Kavir Co., Kashan Kavir, Iran) at room temperature. IR and 1H/13C
NMR spectra were recorded on Thermo Nicolet Nexus 670 FT-IR and 300 MHz Bruker Avance
spectrometers, respectively. The products were characterized by their spectroscopic data and
comparison with the reported data in the literature. All yields refer to isolated pure products.
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TLC was applied for the purity determination of substrates, products and reaction monitoring
over silica gel 60 F254 aluminum sheet.
4.2. Preparation of ZnFe2O4 nanoparticles
ZnFe2O4 nanoparticles were synthesized using the reported method by Sun et al.39 In an agate
mortar, Zn(CH3COO)2·H2O, Fe(NO3)3·9H2O, NaOH, and NaCl were mixed in a molar ratio of
1:2:8:2 and ground together for 50 min. The exothermic reaction started easily after 3 min. The
mixture became pasty and during the reaction its color changed from green to dark orange. In
order to remove the additional salts, this mixture was washed with double-distilled water for
several times. After washing, the obtained combination was dried at 80°C for 2 h. Then the
powders were calcined at 300 °C, 500 °C, 700 °C and 900 °C for 2 h to obtain final
nanoparticles.
4.3. Solvent-free conversion of epoxides to vicinal hydroxythiocyanates with the
NH4SCN/nano ZnFe2O4 system: a general procedure
A mixture of epoxide (1 mmol), NH4SCN (0.076 g, 1 mmol) and nano ZnFe2O4 (0.012 g, 0.05
mmol) was thoroughly ground in a mortar for an appropriate time at room temperature. The
progress of the reaction was monitored by TLC using n-hexane/EtOAc (5:2) as eluent. After
completion of the reaction, the mixture was washed with EtOAc (3 × 5 mL) and the catalyst
nanoparticles were separated by an external magnet. Then the washing solvent was evaporated
under reduced pressure to give the corresponding vicinal hydroxythiocyanate for further
purification by a short-column chromatography over silica gel (75-95%) (Table 2). The
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accumulated nano ZnFe2O4 was washed with ethanol and then with distilled water. The
nanocatalyst was dried and kept for the next run. All products are known compounds and were
identified by comparison of their spectroscopic and physical data with the literature. The 1H and
13C NMR and FT-IR data of the products were in good agreement with those of authentic
samples.18,26,22,23,42,43 These data are presented in the Supplemental Materials.
Spectral data for a selected product:
1
2-Hydroxy-1-phenylethyl thiocyanate (1b): HNMR (CDCl3, 300 MHz) δ 7.46-7.33 (m, 5H,
Ar-H), 4.52 (t, J = 6.6 Hz, 1H, CH-S), 4.19 (d, J = 6.6 Hz, 2H, CH2-OH), 2.16 (bs, 1H, OH); 13C
NMR (CDCl3, 75.5 MHz) δ 135.35 (ArC), 129.44, 129.34, 127.90 (5 × ArCH), 111.11 (SCN),
64.95 (CH2OH), 54.75 (CH-S); IR (max/cm1, neat) 3428, 3031, 2918, 2849, 2153, 1658, 1454,
1063, 760, 699.
Acknowledgements
Financial support of this work by the Research Councils of Payame Noor University is gratefully
acknowledged.
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