Green and Efficient Method for Thiocyanation of Aromatic and Heteroaromatic Compounds Using Cross-linked Poly (4-Vinylpyridine) Supported Thiocyanate Ion as Versatile Reagent and Oxone as Mild Oxidant

Article abstract of DOI:10.1080/10426507.2013.865123

A green and efficient regioselective thiocyanation of indoles, anilines and pyrrole has been achieved via a simple protocol using cross-linked poly (4-vinylpyridine) supported thiocyanate ion, [P₄-VP]SCN, as a versatile polymeric reagent and ox

Full text of DOI:10.1080/10426507.2013.865123

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Green and Efficient Method for
Thiocyanation of Aromatic and
Heteroaromatic Compounds Using Cross-
linked Poly (4-Vinylpyridine) Supported
Thiocyanate Ion as Versatile Reagent and
Oxone as Mild Oxidant
Mohammad Alia, Karimi Zarchia & R. Banihashemia
a Department of Chemistry, College of Science, Yazd University, P. O.
Box 89195-741, Yazd, Iran
Accepted author version posted online: 13 Mar 2014.Published
online: 21 Aug 2014.
To cite this article: Mohammad Ali, Karimi Zarchi & R. Banihashemi (2014) Green and Efficient
Method for Thiocyanation of Aromatic and Heteroaromatic Compounds Using Cross-linked Poly (4-
Vinylpyridine) Supported Thiocyanate Ion as Versatile Reagent and Oxone as Mild Oxidant, Phosphorus,
Sulfur, and Silicon and the Related Elements, 189:9, 1378-1390, DOI: 10.1080/10426507.2013.865123
To link to this article: http://dx.doi.org/10.1080/10426507.2013.865123
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Phosphorus, Sulfur, and Silicon, 189:1378–1390, 2014
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2013.865123
GREEN AND EFFICIENT METHOD FOR THIOCYANATION
OF AROMATIC AND HETEROAROMATIC COMPOUNDS
USING CROSS-LINKED POLY (4-VINYLPYRIDINE)
SUPPORTED THIOCYANATE ION AS VERSATILE
REAGENT AND OXONE AS MILD OXIDANT
Mohammad Ali, Karimi Zarchi,
and R. Banihashemi
Department of Chemistry, College of Science, Yazd University, P. O. Box
89195-741, Yazd, Iran
GRAPHICAL ABSTRACT
Abstract A green and efficient regioselective thiocyanation of indoles, anilines and pyrrole
has been achieved via a simple protocol using cross-linked poly (4-vinylpyridine) supported
thiocyanate ion, [P4-VP]SCN, as a versatile polymeric reagent and oxone as an environmentally
friendly and mild oxidant. Various indoles, anilines, pyrroles, and carbazoles were transformed
into their corresponding aryl thiocyanates in high to excellent yields in a short reaction time.
The present procedure offers advantages such as simple reaction work-up, and the polymeric
reagents can also be regenerated and reused several times without significant loss of their
activity.
Keywords Thiocyanation; oxone; regioselectivity; polymeric reagent; aryl thiocyanate
Received 4 August 2013; accepted 6 November 2013.
Address correspondence to Karimi Zarchi, Department of Chemistry, College of Science, Yazd University,
P. O. Box 89195-741, Yazd, Iran. E-mail: makarimi@yazd.ac.ir
1378

GREEN AND EFFICIENT THIOCYANATION
1379
INTRODUCTION
Arylthiocyanates are well known in the area of organosulfur chemistry1 and have
found widespread applications such as insecticides, biocidal, antiasthmatic, vulcanization
accelerators, and starting materials for the preparation of heterocycles.2–5 The thiocyanation
of aromatics and heteroaromatics is an important carbon-hetero atom bond formation in
organic synthesis and constitutes an interesting group, which could be readily transformed
into other sulfur-bearing functionalities,6,7 especially for producing drugs and pharmaceu-
ticals.8,9 Also, thiocyanate is a versatile synthon which can be readily transferred to other
functional groups such as sulfide,10–13 nitrile,14 thiocarbamate,15,16 thionitrile,17and arylth-
ioesters.18 Therefore, it is important to find new methods for the thiocyanation systems.
Several methods for the thiocyanation of aromatic systems using a variety of
reagents such as bromine/potassium thiocyanate (only for indoles),19 N-thiocyanatosuccin-
imide (only for 5-methoxy-2-methylindole and accompanied by two bisthiocyanates20
trichloroisocyanuric acid/NH4SCN/wet SiO2,21 cerium(IV) ammonium nitrate/NH4SCN,22
acidic montmorillonite K10 clay/NH4SCN,23 iodine/methanol/NH4SCN,24 silica boron
sulfonic acid/H2O2/NH4SCN,25 sodium pertborate/NH4SCN,26 oxone/NH4SCN,27 diethyl
azodicarboxylate,28 diphenylphosphinite ionic liquid,29 potassium peroxydisulfate-
copper(II),30 ferric(III) chloride/NH4SCN,31 acidic alumina/NH4SCN,32 Mn(OAc)3/NH4
SCN33 DDQ/NH4SCN,34 I2O5/NH4SCN,35 and para-toluene sulfuric acid/NH4SCN36 have
been explored. However, these methodologies suffer from one or more drawbacks such
as the less availability or hard preparation of starting materials,19,20 the requirement for a
large excess of oxidizing reagents, low yields for some compounds,22,27 and performances
under certain special conditions.23
Potassium peroxymonosulfate is a cheap and readily accessible oxidizing reagent. It
is commonly referred to as oxone (2KHSO5.KHSO4.K2SO4) and is a versatile and mild
oxidant for the transformation of a wide range of functional groups.37
Recent developments in polymer-supported reactions have led to the propagation
of combinatorial chemistry as a method for the rapid and efficient preparation of novel
functionalized molecules.38 An interesting and fast growing branch of this area is polymer-
supported reagents.39 Although polymeric reagents and scavengers have been used in or-
ganic synthesis for decades, the development of combinatorial and parallel high throughput
synthesis techniques brought this class of reagents to a wider attention. The first compound
collections were based on peptides and oligonucleotides, which were stepwise assembled
on a solid support,40 following the concept developed by Merrifield.41 In recent years,
polymeric reagents, especially anion exchange resins, have been widely applied in organic
transformations.42–61 The advantages of this technique over conventional classical methods
are mild reaction conditions, safe handling, rapid, and very simple work-up. On the other
hand the spent polymeric reagents can usually be regenerated and reused several times
without significant loss of their activity. In addition, many ion-exchange resins, and indeed
reagents supported on them, are commercially available and are relatively inexpensive.
As far as we know there are a few reports in the literature on the application of
polymer-supported thiocyanate ion42–45 but, to the best of our knowledge, there are no
reports on polymer-supported thiocyanate ion for thiocyanation of aromatic or heteroaro-
matic rings. We have recently reported an efficient method for preparation of cross-linked
poly (4-vinylpyridine) supported thiocyanate ion, [P4-VP]SCN, and applied for synthe-
sis of alkyl thiocyanates from alkyl halides44 and for synthesis of aryl thiocyanates via
dediazoniation-thiocyanation of arylamines.45

1380
M. ALI ET AL.
Table 1 Optimization of the reaction conditions for thiocyanation of indole (1mmol) in different solvents and
different molar ratio of [P4-VP] SCN/oxone
Entry
Solvent
[P4-VP]SCN (mmol of SCN ion) Oxone (mmol of KHSO5) Time (min) Yielda (%)
1
2
3
4
5
6
7
8
CCl4
H2O
2.00
2.00
2.00
2.00
2.00
2.00
2.00
2.00
2.00
2.50
1.50
1.50
1.50
1.50
1.50
1.50
1.50
1.50
2.00
1.00
1.50
1.50
120
30
65
30
70
10
120
10
10
10
10
0.0
45
93
96
95
96
0.0
95
74
96
61
C2H5OH
CH3CN
CH3COCH3
CH3OH
CH2Cl2
CH3OH
CH3OH
CH3OH
CH3OH
9
10
11
aIsolated yields.
In this report, we wish to disclose a simple, convenient, and efficient protocol for the
thiocyanation of indoles, anilines, pyrrole, carbazole, and aryl amines using [P4-VP]SCN
as versatile polymeric reagent and oxone as a mild and environmentally friendly oxidant.
RESULTS AND DISCUSSION
In this paper, we report the first procedure for facile and rapid thiocyanation of indoles,
anilines, pyrrole, carbazole, and aryl amines using [P4-VP]SCN as versatile polymeric
reagent and oxone as a mild and environmentally friendly mild oxidant.
Cross-linked poly (4-vinylpyridinium) thiocyanate ion, [P4-VP]SCN, was prepared
according to our previously reported method52 via the reaction of quarternized cross-
linked poly (N-methyl-4-vinylpyridinium) iodide, [P4-VP]I, with an aqueous solution
of KSCN. A variety of activated aromatics such as anilines and heterocyclic aromatics
such as indoles, pyrrole, and carbazole were also subjected to thiocyanation reaction in
methanol.
Since the nature of the solvent influences the rate of reaction, the thiocyanation of
indole (1 mmol) as a model substrate was performed in various solvents such as H2O,
ethanol, methanol, acetone, acetonitrile, CCl4, and CH2Cl2 at room temperature. Accord-
ing to the data presented in Table 1, methanol has selected as the best solvent (entry 6).
One reason for the observed different reaction times could be the solubility of the start-
ing materials in the solvents used in this study. The next step has the optimization of
[P4-VP]SCN/oxone molar ratio in the thiocyanation reaction in methanol were tested. The
results presented in Table 1 showed that the optimized molar ratio of [P4-VP]SCN/oxone
was 2/1.5 (entry 6).
Under the optimized reaction conditions, the thiocyanation of different aromatic and
heteroaromatic compounds such as anilines, indoles, pyrrole, carbazole, and aryl amines
were investigated and the results are summarized in Table 2. The reaction of indole at
room temperature yielded the desired product 3-thiocyanato-1H-indole in 96% yield (Ta-
ble 2, entry 1). The same reaction using N-methyl indole as the starting material gave
3-thiocyanato-N-methyl indole in 98% yield (Table 2, entry 6). The reaction was fur-
ther extended to include other substituted indoles. It was found that 2-methylindole gave

1381

1382

1383

1384

GREEN AND EFFICIENT THIOCYANATION
1385
94% yield of 3-thiocyanato-2-methylindole (Table 2, entry 7). The lower yield is probably
attributed to the steric hindrance of 2-substituted indole.
Indole was chosen as a model substrate and reusability of the polymer was
tested by using [P4-VP]SCN that is recycled first, second, third, and fourth time,
respectively, under identical conditions and the results are summarized in Table 2
(entries 2–5).
After successfully developed the thiocyanation reactions of indoles, we then explored
the reactions of aniline and its derivatives. Aniline is an electron-rich system bearing a
free-amino group. The reaction of [P4-VP]SCN/oxone with aniline performed under the
same condition described above afforded desired product (4-thiocyanatoanilline) in 85%
yield (Table 2, entry 8). Different mono and di-N-substituted anilines were also reacted
with [P4-VP]SCN/oxone, and they all gave high yields (85–88%) of the corresponding
products (Table 2, entries 9–12). As Table 2 reveals, aromatic amino compounds were
readily converted to the mono thiocyanated products with high para-selectivity (Scheme 1
and Table 2, entries 8–12) and the thiocyanato group is selectively added to the para
position of the amino group. These observations are also supported by other reported
methods.21,25–27,33–36 One exception was observed when diphenylamine was subjected to
this approach because mono and di thiocyanated products could be produced (60% mono
and 25% di thiocyanated products were separated) (Table 2, entry 13). The same result has
been reported by Nair et al. when used cerium(IV) ammonium nitrate for thiocyanation
of diphenylamine by ammonium thiocyanate (32% mono and 6% dithiocyanated products
were separated).22 As Table 2 reveals, using indoles (entries 1–7) and carbazole (entry
15) as substrates, the reaction gave unique 3-thiocyano substituted indoles in high yields
(94–98%) and unique 3-thiocyano substituted carbazole in good yield (70%) but, unique
2-thiocyano substituted pyrrole was obtained in 82% isolated yield when, thiocyanation of
pyrrole was treated (entry 14).
The regiochemistry of substitution was achieved by the interpretation of 1H
NMR spectra and their comparison with the spectra and physical data of authentic
samples.
On the other hand, one of the disadvantages of polymeric reagents is their expense,
but in this case, the spent polymeric reagents can in principle be recycled (Scheme 1, step
8) and reused many times (Table 2, entries 2–5). Preparation of the [P4-VP]SCN (steps 1
and 2), regioselective thiocyanation of aromatic and heteroaromatic compounds (steps 3–7)
and regeneration of the polymer (step 7) are shown in Scheme 1.
Table 3 Comparison of the result of the present work for the model reaction with the previous reported method
in literature21,25–27,33–36
Entry
Time (min)
Yield (%)
Mp.
Ref.
33
34
26
36
24
27
35
1
2
3
4
5
6
7
9
120
20
15
45
50
43
20
10
83
97
95
88
85
98
93
96
73–76
105–106
78
—
—
72–73
70–72
73–74
A
A: Present method Table 2 (entry 1).

1386
M. ALI ET AL.
Scheme 1
1
The arylthiocyanate products were characterized by FT-IR; and H- and 13C-NMR
spectroscopy and physical properties were compared known compounds. IR spectrum
showed the characteristic peak of –SCN between 2145–2160 cm−1 and the –C–S stretching
at 642–755 cm−1. The characteristic spectral data of some arylthiocyanate products are
presented as supplemental materials (Table Sh1).

GREEN AND EFFICIENT THIOCYANATION
1387
In Table 3, the result of the present work for the model reaction was compared
with previously reported methods.25–27,33–36 The reaction time in the present method is
shorter than that in the previously reported methods (Table 3, entry 9). This can probably
be attributed to the local concentration of thiocyanate ion species inside the pores of the
polymer.
The reduction potential of oxone and the oxidation potential of indole and ammonium
thiocyanate in anhydrous methanol were determined by Wu and coworkers.27 The reduction
and oxidation potentials of oxone and indole were estimated to be +0.325 V and –1.050 V,
respectively. Yet, the thiocyanate ion exhibited no oxidation potential. So, it might be
assumed that oxone oxidized indole rather than the thiocyanate ion. The oxidation occurs at
the C–C double bond on the hetero-, five-membered ring of indole, giving a cation radical
of indole which was stabilized by a resonance effect. It was followed by nucleophilic attack
of -SCN at the three position. The radical intermediate so formed then undergoes a 3-H-
64
abstraction by OH., that generated from oxone during its reduction, affording the end
product, as depicted in Scheme 2.
Scheme 2
The advantages of this method over conventional classical methods are mild reaction
conditions, safe handling, rapid, and very simple work-up. In addition, there is current
research and general interest in heterogeneous systems because such systems are important
in industry and developing technologies.65
CONCLUSIONS
We have developed an efficient, rapid, experimentally simple method for regiose-
lective thiocyanation of indoles, pyrrole, anilines, and carbazole via a green and simple
protocol using cross-linked poly (4-vinylpyridine) supported thiocyanate ion as versatile
polymeric reagent and oxone as a mild and environmentally friendly oxidant. The spent
polymeric reagent can be easily separated by filtration and can be easily regenerated by
treated with aqueous solution of KSCN and reused for several cycles without significant
loss of their activity.

1388
M. ALI ET AL.
EXPERIMENTAL
Materials and Instruments
Chemicals were either prepared in our laboratory or were purchased from Fluka
(Buchs, Switzerland), Aldrich (Milwaukee, WI), and Merck chemical companies. Poly (4-
vinylpyridine) cross-linked with 2% divinyl benzene (DVB), (white powder, and 100–200
mesh), [P4-VP] 2% DVB, was purchased from Fluka (Buchs, Switzerland). Cross-linked
poly (N-methyl-4-vinylpyridinium) iodide, [P4-VP]I, and cross-linked Poly (N-methyl-
4-vinylpyridine) thiocyanate, [P4-VP]SCN, were synthesized according to our reported
procedures.44 Progress of the reaction was monitored by thin layer chromatography (TLC)
using silica gel Poly Gram SIL G/UV 254 plates (Fluka). All products were characterized
by comparison of their melting point, FT-IR, and in some cases 1H-NMR spectral data,
with those of known samples and all yields refer to the isolated pure products. Melting
points were determined with a Buchi melting point B-540 B.V. CHI apparatus. The Supple-
mental Materials file contains characterization data for the previously known compounds
as products of this reaction.
Preparation of [P4-VP]SCN
Cross-linked poly (N-methyl-4-vinylpyridinium) thiocyanate, [P4-VP]SCN, was syn-
thesized and its capacity was determined according to our reported procedure (Scheme 1).44
The obtained capacity of the polymer was 3.3 mmol of thiocyanate ion per gram of
polymer.
General Procedure for Thiocyanation of Aromatic or Heteroaromatic
Compounds Using [P4-VP]SCN/Oxone
To a suspension of [P4-VP]SCN (625 mg, 2.00 mmol of SCN ion) and an aromatic
or heteroaromatic compound (1 mmol) in methanol (10 mL) was added 924 mg of oxone
(1.5 mmol) and the reaction mixture was stirred at room temperature for the appropriate
time according to Table 2. The progress of the reaction was monitored by TCL [eluent: n-
hexane/ethyl acetate (8/2)]. Then the polymer was separated by filtration and the filtrate was
diluted with water (15 mL) and extracted with dichloromethane (4 × 8 mL). The combined
organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated under
reduced pressure. The resulting crude product was purified by column chromatography on
silica gel (eluted with n-hexane/ethylacetate: 8/2) to afford the corresponding thiocyanated
products.
Regeneration of [P4-VP]SCN
The spent polymer (1.00 g) was added to an excess aqueous solution of KSCN and
was stirred for 24 h at room temperature. The mixture was filtered and washed several times
with distilled water and ethanol and dried overnight under vacuum in the presence of P2O5
at 40 ◦C (Scheme 1, step 8). The regenerated polymer can be reused several cycles without
losing significantly its activity (Table 2, entries 2–5).

GREEN AND EFFICIENT THIOCYANATION
1389
SUPPLEMENTAL MATERIAL
Supplementary data for this article can be accessed on the publisher’s website,
www.tandfonline.com/gpss
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