Versatile catalysis of “natural extract”: oxidation of sulfides and alcohols and ipso-hydroxylation of arylboronic acids

Article abstract of DOI:10.1007/s13738-019-01707-1

Abstract: In the present work, we have described the versatile applications of naturally available inexpensive citrous lemon juice as biocatalyst for controlled oxidation of sulfides and alcohols and ipso-hydroxylation of arylboronic acids using 30% H₂O₂ as a green oxidant. A series of structurally divergent sulfides and benzyl alcohols were oxidized to their corresponding sulfoxides and aldehydes, respectively, with good-to-excellent yields. Similarly, aryl and heteroaryl boronic acids were rapidly, often within minutes, transformed to their corresponding phenols at room temperature. Graphic abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s13738-019-01707-1

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-019-01707-1
ORIGINAL PAPER
Versatile catalysis of “natural extract”: oxidation of sulfdes
and alcohols and ipso‑hydroxylation of arylboronic acids
Apurba Dutta1 · Abdul Aziz Ali1 · Diganta Sarma1
Received: 26 September 2018 / Accepted: 3 June 2019
© Iranian Chemical Society 2019
Abstract
In the present work, we have described the versatile applications of naturally available inexpensive citrous lemon juice as
biocatalyst for controlled oxidation of sulfdes and alcohols and ipso-hydroxylation of arylboronic acids using 30% H2O2 as a
green oxidant. A series of structurally divergent sulfdes and benzyl alcohols were oxidized to their corresponding sulfoxides
and aldehydes, respectively, with good-to-excellent yields. Similarly, aryl and heteroaryl boronic acids were rapidly, often
within minutes, transformed to their corresponding phenols at room temperature.
Graphic abstract
Keywords Green chemistry · Biocatalyst · Lemon juice · Oxidation · Ipso-hydroxylation · Hydrogen peroxide
Introduction
importance in synthetic organic chemistry, pharmaceutical,
biological, and industrial processes (Fig. 1) [4–7]. Thus con-
trolled, environment-friendly catalytic oxidation of sulfdes
to sulfoxides without formation of over-oxidized sulfones
is one of the crucial reactions in organic chemistry. In this
context, lots of works have been projected toward the search
for precise oxidizing agents as well as a natural biomass-
derived catalyst which are both cheap and non-toxic. H2O2,
a cheap and efcient oxidizer, forms only eco-friendly water
as a by-product, and like oxygen, it is considered as one of
the most “green oxidants” till date. However, in sulfoxida-
tion, a number of acid catalysts have been reported such
as HNO3 [8], p-TsOH [9], l-proline [10], boric acid [4],
In the last few decades, “Green Chemistry” has been an
indispensable issue in both academic and industrial felds,
and lacking this approach, industrial chemistry is not sus-
tainable [1–3]. Sulfoxide is a ubiquitous functional group,
and the compounds containing sulfoxide moiety find
* Diganta Sarma
dsarma22@gmail.com; dsarma22@dibru.ac.in
1
Department of Chemistry, Dibrugarh University, Dibrugarh,
Assam 786004, India
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
been paid in the development of an environmentally benign
catalyst system for sulfdes oxidation, alcohols oxidation,
and ipso-hydroxylation of boronic acids to overcome these
drawbacks.
In concord with sustainable chemistry, eforts have been
made for eco-friendly catalysis which has irresistible inter-
est, biodegradable, and used renewable materials as environ-
ment-friendly alternatives [32, 33]. A huge number of biode-
gradable materials, such as chitosan [34], cellulose sulfuric
acid (CSA) [35], water extract of banana (WEB) [36], Water
Extract of Rice Straw Ash (WERSA) [37], egg shell powder
(ESP) [38], natural catalysts [39–41], and a variety of fruit
juices are reported for organic synthesis. Due to their acidic
nature, aqueous fruit juices of lemon [42, 43], pineapple
[44], coconut [45], Acacia concinna [46], Sapindustrifolis-
tus [47], and Tamarindusindica [48] have been found to be
a proper replacement for various homogeneous acid cata-
lysts. Among the naturally available feedstock, lemon juice
is easily available and the main ingredients found in lemon
juice are moisture (85%), carbohydrates (11.2%), citric acid
(5–7%), protein (1%), ascorbic acid (0.5%), fat (0.9%), min-
erals (0.3%), fbers (1.6%), and some other organic acids [49,
50]. The juice is acidic (with pH range 2–3) in nature due to
the presence of citric and ascorbic acids, and thus in organic
reactions, it is used as an acid catalyst. In this work, we have
reported novel and simple methods for controlled oxidation
of sulfdes and alcohols and ipso-hydroxylation of boronic
acids using 30% H2O2 as a green oxidant in the presence of
lemon juice as a natural acid catalyst.
Fig. 1 Biologically active compounds containing sulfoxide moiety
oxalic acid [11], sulfamic acid [12], caprylic acid [13], and
CH3COOH [14] which give good-to-excellent yields, but
all of them are synthetic compounds which are corrosive in
nature and release large amounts of harmful waste materials
to the environment.
Oxidation of alcohols to their corresponding carbonyls
is another important class of organic reactions since the
corresponding carbonyls are versatile key intermediates of
valuable compounds such as pharmaceuticals, agricultural,
and fne chemicals [15–17]. Traditionally alcohol oxidation
was carried out in a number of metal-based stoichiometric
oxidants such as chromium (VI) and manganese (VII) [18,
19]. In view of environmental concern, nowadays, the use
of green oxidant has gained a great deal of attention in aca-
demic and industrial feld. Although there are a large number
of methodologies [20–23] already reported by using H2O2
as cheap and eco-friendly oxidants, most of them required
metal catalyst, additional bases/ligands, and long reaction
times.
Experimental
Preparation of lemon juice
Fresh citrus lemon was collected from Dikom town, Dibru-
garh, Assam. They were washed thoroughly with distilled
water and then cut into smaller pieces and squashed to obtain
the juice. Then the juice was fltered to remove solid mate-
rial, and clear portion of juice was used as a catalyst. The pH
of the extracted lemon juice was found to be 2.93.
In organic syntheses, ipso-hydroxylation of arylbo-
ronic acids to their phenol derivatives is also an important
transformation as phenols are ubiquitous structural unit for
many biologically active molecules, natural products, and
polymers [24, 25]. It was frst reported by Ainley and Chal-
lenger [26] with alkaline hydrogen peroxide, which was
later modifed by Kuivila [27] and Olah [28]. This trans-
formation is green and very simple, but arylboronic acids
with electron-defcient functional groups give low yields
of products, and also alkaline H2O2 can lead to unwanted
side reactions which are the disadvantages of that protocol.
To improve the result, diferent methodologies have already
been reported [29–31] by many research groups, but most of
them used expensive catalyst, organic solvents, and required
long reaction times. Therefore, a great deal of attention has
General procedure for oxidation of sulfdes using
30% H2O2 catalyzed by lemon juice
A mixture of sulfde (1 mmol), 30% H2O2 (4 mmol), and
lemon juice (2 mL) in CH3CN was stirred at room tem-
perature. The progress of the reaction was monitored by
TLC under UV light. After completion of the reaction, the
mixture was extracted with ethyl acetate (3 × 10 mL) and
washed with water (3×10 mL). The combined extract was
dried over anhydrous Na2SO4. The fltrate was concentrated
under reduced pressure. The product was purifed by column
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Journal of the Iranian Chemical Society
chromatography over silica gel using n-hexane/ethyl acetate
of sulfoxide. To study the efect of solvents, we screened
diferent types of organic as well as green solvents in this
reaction and found that CH3CN showed better result than the
others (Table 1, entry 6 vs. entries 11–19). Moreover, the
role of oxidant was also studied, and to our delight, 4 mmol
30% H2O2 was suitable for an excellent yield of sulfoxide
(Table 1, entry 22). Nevertheless, on increasing the 30%
H2O2 to 5 mmol, no signifcant improvement in reaction time
was observed (Table 1, entry 23).
(3:1 v/v) as eluent to get the purifed oxidized product. The
products were then characterized by FTIR and 1H and 13
NMR spectra.
C
General procedure for oxidation of alcohols using
30% H2O2 catalyzed by lemon juice
A mixture of alcohol (1 mmol), 30% H2O2 (5 mmol), and
lemon juice (2 mL) was heated to 80 °C in an oil bath
under vigorous stirring. The progress of the reaction was
monitored by TLC under UV light. After completion of
the reaction, the mixture was extracted with ethyl acetate
(3×10 mL) and washed with water (3×10 mL). The com-
bined extract was dried over anhydrous Na2SO4. The fltrate
was concentrated under reduced pressure. The product was
purifed by column chromatography over silica gel using
n-hexane/ethyl acetate (3:1 v/v) as eluent to get the purifed
oxidized product. The products were confrmed by FTIR,
1H, 13C NMR spectra, and GC–MS analysis.
To extend the scope of the reaction and to generalize
the protocol, we investigated the oxidation of a variety of
organic sulfdes including alkyl phenyl, diphenyl, diben-
zyl, dialkyl, and heterocyclic sulfdes under the optimized
reaction conditions (Table 2). The expected products were
obtained in short reaction times in high yields without the
formation of over-oxidized sulfones. It is notable that under
this reaction condition, allylic double bonds (Table 2, entry
4), and alcoholic groups (Table 2, entry 8) were also tol-
erated. From these two reactions, we can confrm that the
catalyst is selective with respect to functional group.
Further, this methodology was extended to three difer-
ent lemon species found in Dibrugarh district, Assam, India
[1. Common lime (scientifc name: Citrus aurantifolia), 2.
Citron (scientifc name: Citrus medica L.) and 3. Shadoock
(scientifc name: Citrus grandis)], and similar results were
observed toward sulfdes oxidation to sulfoxides at room
temperature.
General procedure for the oxidation of arylboronic
acids to phenols catalyzed by lemon juice
A mixture of arylboronic acid (1 mmol), 30% H2O2
(1 mmol), and lemon juice (2 mL) was stirred at room tem-
perature. The progress of the reaction was monitored by
TLC under UV light. After completion of the reaction, the
mixture was extracted with ethyl acetate (3 × 10 mL) and
washed with water (3×10 mL). The combined extract was
dried over anhydrous Na2SO4. The fltrate was concentrated
under reduced pressure. The product was purifed by column
chromatography over silica gel using n-hexane/ethyl acetate
(3:1 v/v) as eluent to get the purifed oxidized product. The
In order to show the efciency of the present protocol,
our results are compared with the literature reports for the
oxidation of sulfdes (Table 3).
Alcohols oxidation
To expand the versatility of the lemon juice in organic
syntheses, alcohols oxidation was carried out using 30%
H2O2 as green oxidant. A reaction was performed by tak-
ing 4-chlorobenzyl alcohol as model substrate in CH3CN/
H2O solvent media at room temperature for 5 h, but no cor-
responding aldehyde was obtained (Table 4, entry 1). Then
the temperature was increased to 80 °C and interestingly
observed that our desired product was formed with quan-
titative yields within 5 h (Table 4, entry 2). However, with
increasing the temperature to 90 °C, no signifcant improve-
ment of the yields of product was obtained (Table 4, entry
4). To study the efect of solvents, the reaction was carried
out in diferent solvents and in lemon juice alone. Surpris-
ingly, it was found that the reaction gave best results in the
absence of any solvents, thus indicating the role of lemon
juice both as catalyst and solvent (Table 4, entry 5). Fur-
ther, the role of oxidant was also studied and observed that
5 mmol of 30% H2O2 gives the corresponding aldehydes in
higher yields. When the amount of oxidant was increased to
10 mmol, undesired carboxylic acid was formed (Table 4,
1
products were confrmed by FTIR, H, 13C NMR spectra,
and GC–MS analysis.
Results and discussion
In order to establish the best reaction condition, an optimi-
zation study using methyl p-tolyl sulfde as model substrate
was performed. Initially, we examined a series of organic
acids as well as lemon juice which also contain many types
of organic acids (mainly citric acid and ascorbic acid) as
catalysts (Table 1). It was observed that lemon juice showed
good catalytic activity than the other acids even better
than citric acid and ascorbic acid used in these conditions
(Table 1, entries 2, 4). A reaction was performed by taking
a mixture of citric acid and ascorbic acid as catalysts, but
no satisfactory results were obtained (Table 1, entry 5). The
volume of lemon juice was also optimized and found that
2 mL of lemon juice was sufcient for an excellent yield
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Journal of the Iranian Chemical Society
Table 1 Oxidation methyl p-tolyl sulfde with diferent catalysts using 30% H2O2
Entry
Catalyst
Solvent
H2O2 (mmol)
Time (h)
Yielda (%)
1
2
3
4
5
6
7
8
Gallic acid
Citric acid
Uric acid
Ascorbic acid
Citric acid+ascorbic acid
Lemon juiceb
No catalyst
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
MeOH
EtOH
EG
H2O
PEG
DMSO
DMF
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
2
3
4
5
5
6
5
6
6
6
5
6
6
6
6
6
3
3
3
3
4.5
3
3
6
5
3.5
3.5
30
40
00
10
45
65
10
55
65
66
50
55
30
20
15
00
30
00
00
99
99
99
99
Lemon juicec
Lemon juiced
Lemon juicee
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
Lemon juiceb
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
CHCl3
Toluene
CH3CN
CH3CN
CH3CN
CH3CN
Reaction conditions: sulfde (1 mmol) and catalyst (5 mol %) were stirred at room temperature in the given solvent
aIsolated yield
bLemon juice (2 mL)
cLemon juice (1 mL)
dLemon juice (3 mL)
eLemon juice (5 mL)
entry 12), and on the contrary lowering, the amounts of oxi-
dant gives lower yields of product (Table 4, entry 11).
After obtaining the best reaction condition, various ben-
zyl alcohols were investigated using this optimized condition
to confrm the generality and efciency of the present proto-
col (Table 5). Our catalytic system gives good-to-excellent
yields of aldehydes in short reaction period without the for-
mation of undesired carboxylic acid in trace amounts.
our studies with the ipso-hydroxylation of phenyl boronic
acid as model reaction using 1 mmol 30% H2O2 as oxidant
at room temperature without any additional solvents. To our
delight, it was found that our desired phenol was obtained in
almost quantitative yields within 10 min. Since the reaction
was carried out at room temperature in the presence of lower
amounts of oxidant and no additional solvent was used, this
would be the best reaction conditions for this transforma-
tion. To show the versatility of our catalytic system, diferent
types of substituted arylboronic acids were investigated and
found that all the substrates get oxidized to their correspond-
ing phenols within short reaction times (Table 6).
Ipso‑hydroxylation reaction
To extend the application of lemon juice, ipso-hydroxylation
of diferent arylboronic acid was carried out. We initialized
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Journal of the Iranian Chemical Society
Table 2 Oxidation of various
sulfdes with 30% H2O2
catalyzed by lemon juice
Entry
1
Substrates
Products
Time (h)
Yielda (%)
3.5
98
2
3.5
99
3
4
5
5
5
6
90
90
55
6
8
92
7
8
4.5
4
85
96
9
24
2
15
60b
10
12
55
11
12
3.5
3.5
88
92
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Journal of the Iranian Chemical Society
Table 2 (continued)
Reaction conditions: sulfde (1 mmol), 30% H2O2 (4 mmol), and lemon juice (2 mL) were stirred at room
temperature in the CH3CN
aIsolated yields
b80 °C
Table 3 Comparison of present
protocol for the oxidation
of thioanisole with some
previously reported catalytic
system
Entry
Catalyst
Conditions
Time (h)
Yield (%)
References
1
2
3
4
5
6
NBS/H2O2
CH3CN, 35–40 °C
5
93
100
95
92
94
[51]
[52]
[53]
[54]
[55]
This work
Copper(II)complex, TEMPO/H2O2 CH3CN, 20 °C
Fluorous thiourea/H2O2
Borax/H2O2
FeCl3/UHP
Lemon juice/H2O2
4.5
12
6
2
3.5
CH2Cl2, r.t.
CH3OH, r.t.
CH3CN, r.t.
CH3CN, r.t.
99
Table 4 Oxidation 4-chlorobenzyl alcohol with lemon juice using 30% H2O2
Entry
Oxidant (mmol)
Temperature
Solvents
Time (h)
Yielda (%)
1
2
3
4
5
6
7
8
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (5)
H2O2 (2)
H2O2 (10)
r.t.
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
–
EG
DMSO
DMF
tBuOH
EtOAc
–
5
5
5
5
5
5
5
5
5
5
5
5
00
80
00
80b
85
70
60
50
50
70
30
70c
80 °C
60 °C
90 °C
80 °C
80 °C
80 °C
80 °C
80 °C
80 °C
80 °C
80 °C
9
10
11
12
–
Reaction conditions: alcohol (1 mmol), H2O2 (2–10 mmol), and lemon juice (2 ml) were stirred at diferent temperature
aIsolated yield
b<5% of carboxylic acid are obtained
c30% of carboxylic acid are obtained
(present in lemon juice) with H2O2 forms lemon-peroxide
composite (I). Then composite (I) reacts with phenylboronic
acid to form (A) which upon rearrangement and subsequent
water loss produced (B). Finally, hydrolysis of (B) gave the
desired phenol.
Plausible mechanism
A plausible mechanistic pathway for the ipso-hydroxylation
reaction using H2O2 in the presence of lemon juice has been
proposed (Fig. 2). Since lemon juice contains mainly acid
component, the acid interaction or hydrogen bonding of acid
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Journal of the Iranian Chemical Society
Table 5 Oxidation of various benzyl alcohols with 30% H2O2 catalyzed by lemon juice
Entry
Substrates
Products
Time (h)
Yielda (%)
1
5
85
2
3
4
5
5
5
71
74
76
5
6
7
8
10
5
72
65
75
Reaction conditions: alcohols (1 mmol), 30% H2O2 (5 mmol), and lemon juice (2 mL) were stirred at 80 °C
aIsolated yields
knowledge, this is the frst report for sulfdes oxidation
using natural acid as catalyst. Being metal free, having
broad substrate scope, operational simplicity, economic
viability, and excellent yield of the products in shorter
reaction time are some of the advantages of our protocol.
We believe that the present methods will be a more practi-
cal alternative to the other existing procedures.
Conclusion
In conclusion, we have described the fruit juice of citrus
lemon as naturally available inexpensive and environment-
friendly biocatalyst for controlled oxidation of sulfdes
and alcohols and ipso-hydroxylation of arylboronic acids
using 30% H2O2 as a green oxidant. To the best of our
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Journal of the Iranian Chemical Society
Table 6 Lemon juice promoted synthesis of phenol
Entry
Substrates
Products
Time (min)
Yielda (%)
1
10
99
2
15
10
98
98
3
4
5
10
15
98
97
6
7
15
30
95
97
8
9
45
90
97
95
10
35
94
11
12
20
90
96
92
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Journal of the Iranian Chemical Society
Table 6 (continued)
Reaction conditions: boronic acid (1 mmol), 30% H
2O2 (1 mmol), and lemon juice (2 mL) were stirred at room temperature
aIsolated yields
Fig. 2 Plausible reaction
mechanism
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Acknowledgements D.S. is thankful to DST, New Delhi, India, for a
research Grant [No. EMR/2016/002345]. The authors acknowledge the
Department of Science and Technology for fnancial assistance under
DST-FIST program and UGC, New Delhi, for Special Assistance Pro-
gramme (UGC-SAP) to the Department of Chemistry, Dibrugarh Uni-
versity. We acknowledge Dr. Arvind Kumar, Central Salt and Marine
Chemicals Research Institute, Council of Scientifc and Industrial
Research, Gijubhai Badheka Marg, Bhavnagar 364002, Gujarat, India,
and Dr. Ankur Bordoloi Scientist, Nano catalysis, Catalytic Conversion
and Process Division CSIR–Indian institute of petroleum, Mohkampur,
Dehradun-248005, India, for recording the NMR spectra.
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