One-pot synthesis of α-iodoketones from alcohols using ammonium iodide and Oxone in water

Article abstract of DOI:10.1039/c4ra16130k

A novel protocol for the synthesis of α-iodoketones from alcohols has been developed. Using water as the reaction medium, ammonium iodide and Oxone was proven to be an efficient reagent system for this reaction and afforded the corresponding α-iodoketones in moderate to good yields. The generality of this reaction was demonstrated with various secondary alcohols such as benzylic alcohols and aliphatic alcohols (acyclic and cyclic).

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ARTICLE TYPE
One-pot synthesis of α-iodoketones from alcohols using ammonium
®
iodide and Oxone in water
a
a,b
a,b
a
a
Marri Mahender Reddy , Peraka Swamy , Mameda Naresh , Kodumuri Srujana , Chevella Durgaiah ,
a
a,b
Tumula Venkateshwar Rao and Nama Narender *
5
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
DOI: 10.1039/b000000x
9
A novel protocol for the synthesis of α-iodoketones from
interchange of bromo compounds with sodium iodide. Due to
the difficulties in the synthesis and purification of enol silyl
ethers and acetates, in recent years various modified reagents
have been discovered for the synthesis of αꢀiodoketones from
carbonyl compounds using different iodonium donating
alcohols has been developed. Using water as the reaction
®
medium, ammonium iodide and Oxone was proven to be
5
5
6
6
7
7
8
8
0
5
0
5
0
5
0
5
1
0
efficient reagent system for this reaction and afforded the
corresponding α-iodoketones in moderate to good yields.
The generality of this reaction was demonstrated with
various secondary alcohols such as benzylic alcohols and
aliphatic alcohols (acyclic and cyclic).
1
0ꢀ22
systems.
However, most of these methods have one or
more drawbacks, such as use of expensive, hazardous or toxic
reagents, tedious workꢀup procedures and high reaction
temperatures. Therefore, the development of an efficient,
environmentally friendly, atom economic (100% with respect
to iodine) and selective procedure for the direct synthesis of αꢀ
iodoketones is still desirable.
Synthesis of αꢀiodoketones from alcohols instead of
ketones in a single step is a challenging task. Recently,
Barluenga et al. reported the αꢀiodoketones from alcohols
under acidic condition . However, main disadvantage of this
method is the use of strong mineral acid. From the green
chemical point of view there is a need to reduce the chemical
waste and promote simple synthetic methods involving readily
available, inexpensive and less toxic reactants to synthesize αꢀ
iodoketones selectively. To contribute to the development of
an environmentally benign organic chemistry, we are focusing
our research on the replacement of the volatile common
organic reaction media with water (green solvent). As part of
our ongoing research programme to develop ‘greener’
1
2
2
3
3
4
4
5
0
5
0
5
0
5
Strong efforts have been made in the field of green chemistry
to accept methods that are step economic, produce fewer byꢀ
1
products and use less energy and less toxic chemicals. In
particular, the use of water as a solvent for organic synthesis
has become popular and received substantial interest because
water is a green and abundant natural resource which can be
23
2
easily obtained. Moreover, the tandem reactions have also
become a powerful tool for performing several chemical
reactions in only one operation often yielding products with
significantly increased molecular complexity from simple
3
starting materials. The main advantages of tandem reactions
are reduction of overall steps by avoiding isolation of often
highly reactive intermediates, minimization of waste
compared to stepwise reactions, the amount of solvents,
reagents, adsorbents and energy can be dramatically
decreased.
2
4
methods for halogenation, earlier we have reported a method
for the αꢀiodination of carbonyl compounds using NH I–
Oxone system and to the best of our knowledge there are
no reports for the synthesis of αꢀiodoketones from alcohols
using NH I and Oxone . Herein, we report a novel and
It is hard to envision organic chemistry without organoꢀ
halogen compounds because the haloꢀsubstituted organic
compounds are widely used as intermediates in carbonꢀcarbon,
carbonꢀoxygen and carbonꢀnitrogen bond formation reaction.
Moreover, iodinated compounds are generally used in medical
diagnostics as contrast agents or radioactivelyꢀlabelled
4
®
25
®
4
environmentally benign procedure for the direct synthesis of
αꢀiodoketones from alcohols using NH I and Oxone in water
®
4
markers. αꢀIodoketones are among the most versatile
4
without employing any catalyst.
intermediates in organic synthesis and their high reactivity
makes them prone to react with large number of nucleophiles
Initially, we investigated suitable reaction conditions for the
synthesis of αꢀiodoketones using 1ꢀphenylethanol as the model
substrate with NH IꢀOxone reagent system and the results are
described in Table 1. Several solvents (H O, CH OH, EtOH,
isoꢀpropanol, tertꢀbutanol, acetone, CH CN, ethyl acetate,
3
THF, CHCl , CH Cl , CCl and hexane) were investigated and
results revealed that the reaction proceeded only in polar
protic solvents (Table 1). The best results were obtained when
5
to provide a variety of useful compounds. As the iodine atom
®
has poor electrophilic nature, the selective introduction of
iodine into organic molecules has received significant
4
2
3
6
attention among the scientific community. Most of the known
methods of preparing αꢀiodoketones proceed indirectly by
3
2
2
4
7
oxidative iodination of olefins, electrophilic iodination of
8
ketone derivatives (enol ethers, and acetates) or by halogen
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a
water was used as a solvent among others in terms of reaction
yields and time (Table 1, entries 4ꢀ
Table 2 Synthesis of αꢀiodoketones from alcohols
a
Table 1 Optimization of reaction conditions
b
Entry Substrate Time
h)
Product
Yield
(%)
(
OH
O
b
Entry
Solvent
Time (h)
Yield (%)
I
c
1
2
3.5
24
72
10
ꢀ
1
2
3
4
5
6
7
8
9
H
H
H
H
2
2
2
2
O
48
23
35
41
72
20
ꢀ
d
O
24
OH
O
I
e
O
14
Me
Me
f
O
3.5
OH
O
g
CH
3
OH
24
I
g
EtOH
24
3
4
5
6
20
9
OMe
OMe
g
isoꢀPropanol
tertꢀButanol
Acetone
24
ꢀ
OH
O
g
I
24
ꢀ
40
25
g
Br
Br
24
ꢀ
g
OH
O
1
1
1
1
1
1
1
0
1
2
3
4
5
6
CH
3
CN
24
ꢀ
I
g
AcOEt
THF
24
ꢀ
F
F
g
24
ꢀ
OH
O
I
g
CHCl
CH Cl
CCl
Hexane
3
24
ꢀ
6
7
8
24
1
15
66
77
O
2
N
O
2
N
g
2
2
24
ꢀ
OH
O
g
4
24
ꢀ
g
I
24
ꢀ
a
5
4
Reaction conditions: substrate (2 mmol), NH I (2.2 mmol), Oxone®
b 1
OH
O
O
(
2.2 mmol), Solvent (10 ml). products were characterized by H
I
I
I
24
c
d
e
f
NMR, Mass spectra and quantified by GC. RT. 50 °C. 60 °C. 70
g
°
C. Reflux temperature.
3
.8:1
1
6). Next, we examined the temperature effect on this reaction,
OH
O
I
O
10
by varying the reaction temperature from RT to 70 °C a
gradual improvement of reaction yield (23 to 72%) was
observed (Table 1, entries 1ꢀ4). The above results showed that
I
I
9
24
24
72
78
3
.2:1
O
O
OH
6
5
1
0
1
I
I
6
O
5
I
I
1
:2:1.1
O
O
5
4
OH
I
I
1
24
O
79
Scheme 1 Synthesis of αꢀiodoketones.
5
4
I
I
15
the optimum reaction conditions to get the highest yield for
1
.6:2.6:1
this reaction are 1ꢀphenylethanol (1 mmol), NH I (1.1 mmol)
4
2
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DOI: 10.1039/C4RA16130K
O
O
3
5
conditions to afford corresponding αꢀiodoproducts in 61% and
5% yields, along with α,α’ꢀdiiodoproducts in 16% and 17%
yields, respectively (Table 2, entries 8 and 9). Notably, the
acyclic alcohols, such as 2ꢀnonanol, 2ꢀoctanol and 3ꢀoctanol
were rendered the mixture of αꢀiodinated products (two
I
5
4
3
OH
I
O
4
1
1
2
3
24
24
89
80
3
I
I
4
.4:3.5:1
40 monoiodinated regiomers and α,α’ꢀdiiodoproducts) in > 77%
yield (Table 2, entries 10ꢀ13). For example, 2ꢀnonanol
delivered the 1ꢀiodoꢀ2ꢀnonanone, 3ꢀiodoꢀ2ꢀnonanone and 1,3ꢀ
diiodoꢀ2ꢀnonanone in 19%, 38% and 21% yields, respectively
Table 2, entry 10). 4ꢀPhenylꢀ2ꢀbutanol was also provided the
45 mixture of αꢀiodinated products in 80% yield (Table 2, entry
3).
In a blank experiment, no reaction occurred between
O
O
Ph
Ph
OH
I
I
(
O
Ph
Ph
1
I
I
3
.2:3.8:1
®
acetophenone and NH I without Oxone (oxidant) under
4
a
4
Reaction conditions: substrate (2 mmol), NH I (2.2 mmol), Oxone®
1
similar reaction conditions. Thus the role played by the
b
(
2.2 mmol), Water (10 ml), 70 °C. products were characterized by H
®
5
5
6
0
5
0
Oxone is justified. In absence of NH I also we did not
4
NMR, Mass spectra and quantified by GC.
®
observe any reaction between Oxone and alcohol. Based on
®
2
3,
and Oxone (1.1 mmol) in water (10 ml) at 70 °C.
the above experimental observations and literature reports
25,26
5
With the optimized conditions in hand, the scope and
limitations of the method was explored (scheme 1) with a
variety of secondary alcohols (benzylic and aliphatic secondary
alcohols) and the results are summarized in Table 2. 1ꢀ
Phenylethanol produced the corresponding αꢀiodoproduct in
high yield (Table 2, entry 1). In order to determine the
influence of substitution on aromatic ring of 1ꢀphenylethanol
on the reaction path with this reagent system, we studied the
reaction with different substitutions (Table 2, entries 2ꢀ6).
Moderately activating group present on aromatic ring of 1ꢀ
phenylethanol i.e. 1ꢀ(4ꢀmethylphenyl)ethanol provided lower
yield (10%) (Table 2, entry 2). Whereas, highly activated 1ꢀ
, we propose a probable reaction mechanism for the
formation of αꢀiodoketones from alcohols is shown in Scheme
2. It is assumed that the I (NH I) is oxidized with Oxone to
Θ
®
4
⊕
⊕
generate the I (HOI) in situ. I (HOI) plays multiple roles in
this reaction. First, it acts as the oxidizing agent to convert
®
1
1
2
2
3
0
5
0
5
0
alcohol into ketone via intermediate A. Then, Oxone oxidizes
Θ
⊕
⊕
the generated I (NH I) to I (HOI), which (I (HOI)) acts as
4
iodinating agent and further reacts with enol form of carbonyl
compound to afford the corresponding αꢀiodinated product.
Conclusions
In conclusion, we have developed an efficient and green
phenylethanol i.e. 1ꢀ(3ꢀmethoxyphenyl)ethanol gave
a
protocol for the synthesis of αꢀiodoketones directly from
complex mixture of unidentified products, which contained
virtually no αꢀiodoproduct (Table 2, entry 3). Halo substituted
1ꢀphenylethanols such as 1ꢀ(4ꢀbromophenyl)ethanol and 1ꢀ(4ꢀ
fluorophenyl)ethanol were gave the corresponding αꢀiodinated
products in 40% and 25% yields, respectively (Table 2, entries
®
6
7
7
5
0
5
secondary alcohols using NH I and Oxone without metal or
4
mineral acid catalyst in aqueous media. Various secondary
alcohols, such as benzylic alcohols and aliphatic alcohols
(acyclic and cyclic) can be oxidizedꢀiodinated by this reagent
system under mild conditions and affording the corresponding
αꢀiodoproducts in moderate to good yields. Remarkably, the
process conducted in water (green solvent) and offers several
advantages, such as commercial availability of the reagents,
simple reaction conditions, high atom economy (100% with
respect to iodine), good yields, easier setup/workꢀup
procedures and environmentally friendly nature makes our
method more valuable from preparative point of view.
4
and 5). Highly deactivated 1ꢀ(4ꢀnitrophenyl)ethanol also
furnished lower yield of the corresponding product (Table 2,
entry 6). Interestingly, 1ꢀphenylpropanol showed good
reactivity with this reagent system and yielded the
corresponding αꢀiodoproduct in good yield (66%) within 1 h
(
Table 2, entry 7).
Further, we investigated the efficiency of this method with
aliphatic alcohols. In case of cyclic alcohols such as,
cycloheptanol and cyclooctanol were reacted under the similar
Experimental section
®
General procedure for the synthesis of αꢀiodoketones: Oxone
(2.2 mmol) was slowly added to a well stirred solution of
80
NH I (2.2 mmol) and alcohol (2 mmol) in water (10 ml) and
4
the reaction mixture was allowed to stir at 70 °C. After
disappearance of the alcohol (reaction was monitored by TLC)
or after the appropriate time, the organic product mixture was
extracted with DCM (3 x 25 mL). The organic layer was
washed with 5% aqueous sodium thiosulfate solution (10 mL)
and dried over anhydrous Na SO . The solvent was removed
85
2
4
in vacuo and the residue was purified by column
chromatography over silica gel using nꢀhexaneꢀethyl acetate
as eluent to give desired products. All the products were
Scheme 2 The probable reaction mechanism for the formation of αꢀ
iodoketones from alcohols.
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1
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Acknowledgements
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We thank the CSIR Network project CSCꢀ0125 for financial
support. M.M.R., M.N. and Ch.D acknowledge the financial
support from CSIR, India in the form of fellowships. P.S. and
K.S. acknowledge the financial support from UGC, India in
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a
I&PC Division, CSIRꢀIndian Institute of Chemical Technology,
Hyderabad 500 007, India. Eꢀmail: narendern33@yahoo.co.in; Fax:
91ꢀ40ꢀ27160387/27160757; Tel: +91ꢀ40ꢀ27191703
Academy of Scientific and Innovative Research, India
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†
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Electronic Supplementary Information (ESI) available:
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