A simple and efficient iodination of aromatic compounds using I2/Choline Chloride/K2S2O8

Article abstract of DOI:10.14233/ajchem.2018.21308

A simple and efficient method for the iodination of aromatic compounds has been achieved in the presence of molecular iodine, choline chloride and potassium peroxodisulfate at 65 °C in acetonitrile. The rate of conversion of aromatic compounds into iodoaromatic compounds was promoted by in situ formed choline peroxodisulfate. This protocol provides an efficient access to iodoarenes with operational simplicity, good functional group tolerance and a moderate to good product yield.

Full text of DOI:10.14233/ajchem.2018.21308

Asian Journal of Chemistry; Vol. 30, No. 7 (2018), 1659-1663
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2018.21308
A Simple and Efficient Iodination of Aromatic Compounds Using I
2
/Choline Chloride/K
2 2
S O
8
1
2,*
D. PARTHIBAN and R. JOEL KARUNAKARAN
1
2
P.G. & Research Department of Chemistry, Arignar Anna Government Arts College, Cheyyar-604 407, India
Department of Chemistry, Madras Christian College, Tambaram, Chennai-600 059, India
*
Corresponding author: E-mail: rjkmcc@yahoo.com
Received: 28 February 2018; Accepted: 25 April 2018;
Published online: 31 May 2018;
AJC-18950
A simple and efficient method for the iodination of aromatic compounds has been achieved in the presence of molecular iodine, choline
chloride and potassium peroxodisulfate at 65 °C in acetonitrile. The rate of conversion of aromatic compounds into iodoaromatic compounds
was promoted by in situ formed choline peroxodisulfate. This protocol provides an efficient access to iodoarenes with operational simplicity,
good functional group tolerance and a moderate to good product yield.
Keywords: Iodination, Choline chloride, Potassium peroxodisulfate, Choline peroxodisulfate, Molecular iodine.
Pd(OAc)
milling [20], I
2
[19], I
2
/LiOtBu/1,10-phenanthroline [6], NIS/Ball
/CsOAc/NaHCO [21].
INTRODUCTION
2
/Pd(OAc)
2
3
Aryl iodides are important class of compounds for the
synthesis of various pharmaceutical and bioactive compounds
1]. A large amount of research have been devoted to the
However, most of the described reactions in the literature
require one or some of the following conditions: an excess of
the reagent or strong oxidizing agent, hazardous toxic solvents,
elevated temperature, the use of expensive catalysts that need
to be prepared prior to use, corrosive mineral acids, expensive
Lewis acids, the use of corrosive and moisture-sensitive iodine
monochloride, iodine vapour irritant in solvent free conditions.
Moreover, the practical application of most of these reagents
suffers from disadvantages such as low regioselectivity, long
reaction times, low yields and tedious work-up. Therefore,
development of new methods for the preparation of iodo-
aromatic compounds, in order to increase the regioselectivity,
yields of products and to reduce reaction times, is still in great
demand.
[
synthesis of iodoaromtic compounds, including electrophilic
aromatic halogenations [2], the Sandmeyer reaction [3] or
ortho-lithiation [4]. They are the most reactive intermediates
for various cross-coupling reactions such as Heck reactions,
Still and Negishi cross couplings reactions and especially
useful for formation of carbon-carbon and carbon-heteroatom
bonds in the preparation of ethylenic and acetylenic comp-
ounds on the basis of catalytic condensations [5]. Though direct
iodination of arenes is logically more attractive, however, the
iodofunctionalization of aromatics and heteroarenes is fre-
quently not straightforward due to the weak electrophilic nature
of the iodonium ion and relatively weak bond strength of C–I
compared to C–Br and C–Cl. Therefore the direct iodination
of arenes with molecular iodine under mild conditions requires
an oxidizing agent to activate less active molecular iodine to
Peroxodisulfate compounds like K
2
S
2
O
8
, Na
2
S
2
O
8
and
(NH ) S O
4 2 2 8
are widely used for the oxidation of various organic
compounds, because the peroxodisulfate ions are an excellent,
versatile oxidant and possess high oxidation potential [22].
But these reagents imposes certain limitations such as high
activation energy (30 kcal/mol), use of strong mineral acids
and toxic transition metals catalyst for hemolysis of peroxo-
+
the more reactive species with an I character. Many oxidizing
+
agents have been considered for formation of I like species
either in situ or as stable isolable intermediates. Some examples
2-
·–
4
of iodinating agents are: I
HIO /grinding [9], I /Bi(NO
11], NIS/In(OTf) [12], I /silver nitrate [13], NIS/CF
14], N-iodosaccharin [15], hydroxyl radicals/nanocrystalline
/I [16], N-chlorosuccinimide and sodium iodide [17].
Recent methods for iodination of aromatic compounds includes
the reactions catalyzed by NIS/Pd(OAc) [18], KIO /K
2
/CuBr
2
[6], CsI
3
[7], KF/I
2
[8], I
/TMOF
CO
2
/
disulfate ion (S
O
2 8
) into sulfate radical (SO ) [23].
3
2
3
)
3
·5H
2
O-BiCl
3
[10], I
2
The modified peroxodisulfate compounds have becoming
promising compounds for various organic transformations. For
example, iodination of various aromatic compounds containing
[
[
3
2
3
2
H
CeO
2
2
activating and deactivating functional groups by I
(triphenylphosphonium)-2-butene peroxodisulfate [24], I
butyl-triphenylphosphonium peroxodisulfate [25], I /tetra-
2
/1,4-bis-
2
/n-
2
3
S
2 2
8
O /
2

1
660 Parthiban et al.
Asian J. Chem.
1
3
butylammonium peroxodisulfate [26], I
phosphonium peroxomonosulfate [27], I
phosphonium peroxydisulfate [28], KI/ammonium peroxo-
disulfate [29] are few of them to mention. In continuation to
our search for simple non-hazardous methods for the organic
transformations, especially for synthesis of iodinated compound
2
/benzyltriphenyl-
/methyltriphenyl-
J = 8.8 Hz, 2H), 7.51 (d, J = 8.4 Hz, 2H); C NMR (100
MHz, CDCl ): δ 82.85, 117.51, 138.19, 155.26; Mass m/z:
calcd. for C OI: 219.02; found: 219.04.
c) 4-Iodo-2-methyl phenol: m.p.: 64-66 °C; H NMR
(400 MHz, CDCl ): 2.09 (s, 3H), 5.33 (broad, 1H), 6.71 (d, J
= 8.4, 1H), 6.95 (d, J = 8.4, 1H), 7.04 (s, 1H) C NMR (100
MHz, CDCl ): 15.78, 115.34, 121.04, 124.44, 125.50, 129.68,
153.77; Mass m/z: calcd. for C OI: 234.03; found: 234.97.
d) 2-Chloro-4-iodoaniline: White crystalline solid, mp
2
3
6
H
5
1
3
1
3
[
30-33]. In this article, we wish to report the use of molecular
3
iodine/choline chloride/potassium peroxodisulfate system as
an excellent iodinating agent for the iodination of both activated
and deactivated aromatic compounds.
H
7 7
1
65-67 (Lit. 68–70) [33]; H NMR (400 MHz, CDCl
3
): δ4.15
(
1
1
br, 2H), 6.49 (d, J = 8.4 Hz, 1H), 7.28 (q, 1H), 7.51 (d, J =
EXPERIMENTAL
13
.8 Hz, 1H); C NMR (100 MHz, CDCl
3
): δ 117.33, 120.23,
NClI: 253.47;
36.33, 137.17, 142.74; Mass m/z: calcd. for C
H
6 5
Choline chloride, potassium peroxodisulfate, aromatic
compounds such as phenol, aniline, anisole, toluene etc.
and solvents like ethyl acetate, acetone, petroleum ether and
dichloromethane are purchased from SD fine chemicals, India.
Melting points were measured on Deep vision apparatus in
open capillary tubes, values are reported uncorrected.Thin
layer chromatography was carried out on pre-coated sheets of
silica gel containing 60 F254 indicator (Merck, Darmstadt,
Germany). Column chromatography was performed with silica
found: 253.08.
e) 2-Iodo-4-chloroaniline: Brown solid, m.p.: 41 °C (lit.
1
3
2
1
8
8–40 °C) [33]; H NMR (400 MHz, CDCl
3
): δ 4.23 (brs,
H), 6.71 (d, J = 8.6Hz, 1H), 7.18 (dd, J = 2.4 Hz and 8.6 Hz,
13
H), 7.48 (d, J = 2.4Hz, 1H); C NMR (100 MHz, CDCl
4.7, 115.5, 125.3, 129.2, 138.5, 144.3; Mass m/z: calcd. for
NClI: 253.47; found: 253.08.
f) 2-Iodo-4-nitroaniline: Yellow solid, m.p.: 98 °C (lit.
3
): δ
C
6
H
5
1
1
99–100 °C) [33]; H NMR (400 MHz, CDCl ): δ 7.07 (d, J =
3
gel (60-120 mesh; SD Fine). H NMR spectra were recorded
7
Hz, 1H), 8.06 (dd, J = 2Hz and 7 Hz, 1H), 8.67 (d, J = 2 Hz,
on 400 MHz Brucker Advance instrument in CDCl
3
solvent;
C NMR spectra were recorded on 100 MHz BruckerAdvance
instrument in CDCl solvent, chemical shifts (δ) are expressed
13
13
1H); C NMR (100 MHz, CDCl ): δ 83.1, 115.2, 126.6, 135.9,
3
1
2
43.8, 163.4; Mass m/z: calcd. for C
65.11.
H
6 5
N
2
O I: 264.02; found:
2
3
in ppm value relative to the internal standard TMS. FT-IR of all
the samples was recorded on a Brucker alpha-P spectrophoto-
meter. Mass spectra were recorded on a JEOL GC Mate II
mass spectrometer.
General procedure for iodination of aromatic compo-
unds: To a solution of aromatic compound (10 mmol) in
acetonitrile (5 mL) in a 100 mL round-bottomed flask with a
magnetic bar was added choline chloride(10 mmol), potassium
peroxodisulfate (10 mmol) and iodine (15 mmol). The reaction
mixture was stirred for the appropriate time at 65 °C. The
progress of the reaction was monitored by TLC. The reaction
mixture was poured into aqueous sodium thiosulfate solution
g) 4-Iodoanisole: Yellow solid, m.p.: 51 °C (mp 46–48
1
°
2
1
C) [33]; H NMR (400 MHz, CDCl ): δ 3.71 (s, 3H), 6.65 (d,
3
13
H), 7.48 (d, 2H); C NMR (100 MHz, CDCl
16.5, 138.3, 159.1; Mass m/z: Calcd for C
3
): δ 55.3, 82.6,
7 7
H OI: 234.03;
Found 233.11.
1
h) 4-Iodotoluene: Brown solid, m.p.: 33-35 °C; H NMR
(
400 MHz, CDCl ): δ/ppm 2.22 (s, 3H), 6.83 (d, J = 8.0 Hz,
3
13
2
2
2
H), 7.48 (d, J = 8.0 Hz, 2H), C NMR (100 MHz, CDCl
3
): δ
I:
1.28, 90.55, 131.37, 137.37; Mass m/z: calcd. for C
7
H
7
18.03; found: 218.08.
i) 2-Chloro-4-iodotoluene: Off-white solid, m.p.: 83-85
1
°
8
(
1
C; H NMR (400 MHz, CDCl ): δ 2.26 (s, 3H), 6.86 (d, J =
3
(
1 mol/L) in order to remove unreacted iodine and extracted
13
.0 Hz, 1H, ), 7.39 (q, 1H), 7.76 (d, J = 1.2 Hz, 1H) C NMR
): δ 19.61, 90.06, 132.06, 135.00, 135.78,
36.92; Mass m/z: calcd. for C ClI: 252.48; found: 251.05.
j) 4-Iodo-o-xylene: Brown solid, m.p.: 69-71 °C; H NMR
400 MHz, CDCl ): δ 2.15 (s, 6H), 6.79 (d, J = 8.0 Hz, 1H, ),
with ethyl acetoacetate (10 mL, 3 times). Organic layer is dried
over anhydrous sodium sulphate. Evaporation of the solvent
under vacuum followed by column chromatography on silica
gel gave the corresponding iodinated compounds (Scheme-I).
100 MHz, CDCl
3
H
7 6
1
(
7
3
13
.35 (d, J = 8.0 Hz, 1H), 7.40 (s, 1H); C NMR (100 MHz,
): δ 19.24, 90.55, 131.24, 134.53, 135.13, 137.41,
138.89; Mass m/z: calcd. for C I: 232.06; found: 231.33.
k) 4-Iodo-m-xylene: Brown solid, m.p.: 71-72 °C; H
NMR (400 MHz, CDCl ): δ 2.23 (s, 3H), 2.35 (s, 3H), 6.63 (d,
J = 8.1 Hz, 1H, ), 7.02 (s, 1H), 7.61 (d, J = 8.1 Hz, 1H); C
NMR (100 MHz, CDCl ): δ 20.98, 28.04, 97.17, 128.45,
130.86, 138.11, 138.72, 141.059; Mass m/z: calcd. for C I:
32.06; found: 232.06.
l) 3-Iodobenzoic acid:White solid, m.p.: 189 °C (lit.187)
H
H
CDCl
3
I /Choline chloride/K S O
2
2
2
8
H
8 9
1
I
Acetonitrile, 65 °C, 120 min
R
R
3
13
Scheme-I
3
Spectral data
a) 4-Iodoaniline: Brown solid, m.p.: 53–55 °C (lit. 55–
8
H
9
2
1
5
6
(
6.5 °C) [34]; H NMR (400 MHz, CDCl
.44 (d, J = 8.4 Hz, 2H), 7.38 (d, J = 8.4 Hz, 2H); C NMR
): δ 79.41, 117.33, 137.92, 146.08; Mass
NI: 219.02; found: 221.08.
3
): δ3.46 (br, 2H),
1
13
[33]; H NMR (400 MHz, CDCl
3
): δ 5.11 (s, broad), 7.23 (t, J
=
8.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 8.0 Hz,
100 MHz, CDCl
m/z: calcd. for C
3
13
1
1
H), 8.45 (s, 1H),; C NMR (100 MHz, CDCl
29.34, 130.18, 131.22, 139.07, 142.58, 169.84; Mass m/z:
I: 248.02; found: 248.00.
3
): δ 93.83,
6
H
6
b) 4-Iodophenol: Brown solid, m.p.: 92-93 °C (lit. 92
1
calcd. for C
H
7 5
O
2
°
C) [33]; H NMR (400 MHz, CDCl ): δ 5.20 (s, 1H), 6.62 (d,
3

Vol. 30, No. 7 (2018)
A Simple and Efficient Iodination of Aromatic Compounds Using I
2
/Choline Chloride/K
2
S
2
8
O 1661
m) 1-Chloro-4-iodo-benzene: Yellowish powder, m.p.:
6, Table-1). Acetonitrile was found to be the good choice for
iodination with optimum yield of 93 % of desired product
(entry 4, Table-1).
Then we performed the reaction of aniline (10 mmol) in
the presence of varying amounts of molecular iodine, choline
chloride and potassium peroxodisulfate. We have realized that
the molar ratio of 1.0/1.0/1.0/1.5 for aromatic substrate/iodine/
choline chloride/oxidant was satisfactory, giving products in
good yields at reflux temperature (entry 5, Table-2).
1
5
4 °C (lit.56 °C) [33]; H NMR (400 MHz, CDCl
3
): δ 7.05 (d,
J = 8.0 Hz, 2H), 7.57 (d, J = 8.0 Hz, 2H); C NMR (100
MHz, CDCl ): δ 91.19, 130.18, 134.24, 138.42; Mass m/z:
calcd. for C ClI: 238.45; found: 238.17.
n) 1-Bromo 4-iodo-benzene: White solid, m.p.: 88-89 °C
13
3
H
6 4
1
(
8
lit.90 °C) [33]; H NMR (400 MHz, CDCl
3
): δ 7.20 (d, J =
.0 Hz, 2H), 7.51 (d, J = 8.0 Hz, 2H); C NMR (100 MHz,
): δ 92.06, 122.23, 133.14, 138.81; Mass m/z: calcd. for
BrI: 282.90; found: 282.20.
13
CDCl
3
C
6
H
4
TABLE-2
RESULTS AND DISCUSSION
In this paper, we are reporting the use of choline chloride/
EFFECT OF MOLE RATIO OF SUBSTRATE, CHOLINE
CHLORIDE, POTASSIUM PEROXODISULFATE AND
MOLECULAR IODINE
potassium peroxodisulfate as a highly efficient oxidant for the
iodination of activated as well as deactivated aromatic comp-
ounds by molecular iodine. The iodination of aromatic comp-
ounds with this reagent was investigated in acetonitrile under
reflux conditions. Iodination takes place by oxidation of
molecular iodine into electrophilic iodonium cation radical
Substrate/choline
chloride/oxidant/iodine
Yield
(%)
56
73
75
53
92
43
Trace
Entry
Solvent
CH CN
Time
1
2
3
4
5
6
7
1.0/1.0/0.5/1.0
1.0/1.0/1.0/1.0
1.0/1.0/1.5/1.0
1.0/1.0/1.0/0.5
1.0/1.0/1.0/1.5
1.0/––/1.0/1.5
1.0/1.0/––/1.5
2.5
2.5
2.5
2.5
2.5
2.5
2.5
3
CH CN
3
CH CN
3
CH CN
3
CH CN
3
•+
(
2
I ) by in situ formed choline peroxodisulfate. The in situ
CH CN
3
formation of choline peroxodisulfate was supported by the
work reported by Gadilohar et al. [35] (Scheme-II). They
found that choline peroxodisulfate is quite stable when stored
below 10 °C in the absence of light for months without loss of
its activity and it is soluble in polar solvents such as methanol,
ethanol, acetonitrile, but insoluble in solvents such as hexane
and diethyl ether.
Our initial experiment was to optimize the reaction condition,
so we examined the iodination of aniline as a model substrate
in the presence of molecular iodine as iodinating reagent and
choline chloride/potassium peroxodisulfate as oxidizing agent
in different solvent such as water, dichloromethane, ethanol,
methanol, acetone, acetonitrile at reflux condition in order to
study the influence of solvent (Table-1). Iodination of aniline
CH CN
3
We investigated iodination reaction of all other activated
and deactivated aromatic compounds in the optimized condi-
tions using I /choline chloride/potassium peroxodisulfate
2
iodinating system.The absence of any side products in TLC
confirmed that the reaction was very clean.A variety of commer-
cially available aniline, phenol, methyl and methoxy aromatic
compounds were subjected to the reaction with molecular
iodine and potassium peroxodisulfate in the presence of choline
chloride at 65 °C. Iodination of aniline derivatives took place
with high yield at 65 °C with short reaction times, between
6
0- 90 min (entry a; Table-3) and 90-120 min (entries d, e and
f; Table-3). Surprisingly, iodination of phenol derivatives
proceeded in 90-120 min at 65 °C (entry b,c; Table-3), whereas
reaction of methoxy and methyl derivatives proceeded in 150-
with I /choline peroxodisulfate was unsuccessful in water and
2
also in dichloromethane (entry 1, 2; Table-1). On the other hand,
we performed same reaction in methanol and ethanol, unfortu-
nately, rate of reaction in methanol and ethanol was also dis-
appointingly sluggish even at elevated temperatures (entry 3,
2
10 min with good yield (entry g,h,i,j,k; Table-3). Iodination
of benzoic acid, chlorobenzene and bromobenzene required
refluxing for 180-300 min with moderate yield (entry l, m, n;
Table-3). Thus highest yields were observed with nucleophilic
arenes, such as aniline, phenol, anisole and moderate yields
were observed electron-poor arenes such as benzoic acid, chloro-
phenol.
Plausible mechanism: We have proposed a plausible mecha-
nism for iodination of aromatic compounds by molecular
iodine and choline chloride/potassium peroxodisulfate; by
homolytic cleavage under the influence of heat, in situ formed
choline peroxodisulfate readily forms choline sulphate radical
5
, Table-1). Then, we attempted iodination in acetone, we
obtained desired product in 62 %, it was also not encouraging
because of longer reaction time and poor product yield (entry
TABLE-1
OPTIMIZATION OF IODINATION REACTION
S. No.
Solvent
Water
Dichloromethane
Methanol
Acetonitrile
Ethanol
Time (h)
6.0
6.0
4.0
2.5
4.0
3.5
4.0
Temp. (°C)
Yield (%)
1
2
3
4
5
6
7
65
65
65
65
65
65
65
–
23
31
93
57
62
47
[
[
1], which can be easily converted into choline sulphate anion
4] by one electron transfer from molecular iodine [3], so that
molecular iodine is oxidized to iodonium cation radical [4].
Acetone
DMSO
O
O
O
O
O K
O
Acetonitrile
stirring
O
S
O
O
N
K
O
O
S
+
O
S
N
N
OH
+
2KCl
2
HO
O
S
O
HO
Cl
O
O
Choline chloride
Choline peroxodisulfate
Scheme-II

1
662 Parthiban et al.
Asian J. Chem.
TABLE-3
Yield
(%)
Time
Time
(min)
Yield
(%)
Entry
a
Substrate
Product
Entry
Substrate
Product
(
min)
NH2
CH3
NH2
OH
CH3
90
94
h
180
71
67
69
I
I
OH
CH3
CH3
Cl
Cl
b
c
90
92
86
i
j
180
210
I
I
OH
CH3
OH
CH3
CH3
CH3
CH3
CH3
120
I
I
NH2
CH3
Cl
CH3
NH2
Cl
d
120
81
k
210
65
CH3
I
CH3
I
NH2
NH2
COOH
COOH
I
I
e
f
120
120
150
86
76
73
l
180
240
300
61
57
I
Cl
NH2
Cl
NH2
Cl
Cl
Br
m
NO2
NO2
I
OCH3
Br
OCH3
g
n
51
I
I
O
S
O
The nucleophilic attack of iodonium cation radical on aromatic
substrate produces an intermediate [6], which rapidly oxidized
to iodinated aromatic compounds. The rate of the reaction may
further accelerated by in situ formed HI acid (Scheme-III).
N
O
O
+
I
I
2
+
Z
N
O
S
O
2
HO
O
HO
O
[
1]
[2]
[3]
[4]
Conclusion
Z
I
Z
In conclusion, a simple procedure is developed for the
iodination of activated as well as deactivated aromatic com-
pounds by molecular iodine in the presence of choline chloride/
I
I
-I
R
- H
R
R
I
H
potassium peroxodisulfate. I /choline chloride/potassium
2
[
5]
[3]
[
6]
[7]
peroxodisulfate system is a mild, efficient, inexpensive iodi-
nating agent. The methodology involves the in situ generation
Scheme-III

Vol. 30, No. 7 (2018)
A Simple and Efficient Iodination of Aromatic Compounds Using I
2
/Choline Chloride/K
2
S
2
8
O 1663
1
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•
+
cation radical (I ), which acts as the electrophile for the
2
iodination, moreover HI formed as side product will enhance
the rate of conversion. A remarkable feature of this system is
that harsh reaction condition such as high temperature, toxic
transition metal catalyst and strong oxidizer are not required,
toxic volatile solvents are not used as well as not produced
during the reaction, furthermore the reagent can be easily
prepared.
1
1
1
1
1
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