Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant

Article abstract of DOI:10.1039/c7gc01416c

A highly selective synthesis of sulfoxides from alkenes and thiols was established by visible-light photoredox catalysis at room temperature. This metal-free transformation protocol, which uses inexpensive Rose Bengal as the photocatalyst and air as the green oxidant, opens a new door toward the facile and practical construction of sulfoxides.

Full text of DOI:10.1039/c7gc01416c

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Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using
air as the oxidant†
Huanhuan Cui, Wei Wei*, Daoshan Yang, Yulong Zhang, Huijuan Zhao, Leilei Wang, Hua Wang*
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
5
DOI: 10.1039/b000000x
and oxidant under nitrogen atmosphere.19 Gracefully successive
A highly selective synthesis of sulfoxides from alkenes and
50 as these metal-free methods could be, there is still a great demand
for the development of more mild, economic, efficient, and
environmentally-benign methods to selectively construct
sulfoxides.
thiols was established by visible-light photoredox catalysis at
room temperature. This metal-free transformation protocol,
which uses inexpensive Rose Bengal as the photocatalyst and
10 air as the green oxidant, opens a new door toward the facile
and practical construction of sulfoxides.
Visible-light has long been recognized as an ideal chemical
55 energy to promote the organic synthetic transformations due to its
clean, inexpensive, and renewable features. In recent years,
especially after 2008, visible-light photoredox catalysis has
emerged as a highly versatile and powerful tool for the
construction of various valuable organic compounds via the
60 formation of C-C and C-heteroatom bonds under the mild
conditions.20 Very recently, we also presented a new visible-light
induced oxysulfonylation of alkenes with sulfinic acids for the
synthesis of β-ketosulfones with the assistance of excess amounts
of THBP.21 Molecular oxygen is a green oxidant and oxygen
65 source in view of economic and environmental points. Thus,
developing a dioxygen activation by photoredox catalysis for the
Sulfoxides are extremely valuable organic compounds, which are
not only frequently found in a large number of nature products
and pharmacologically active molecules,1 but also serve as the
15 versatile building blocks for the construction of various important
chemicals2 and therapeutic agents such as antiulcer,3 antifungal4
and antiatherosclerotic5 agents in both academic and industrial
communities. Consequently, sulfoxide functionality strongly
attracts synthetic pursuit of chemists owing to its structural
20 diversity and remarkable biological functions. Traditionally, the
approaches for the synthesis of sulfoxides rely heavily on the
oxidation of sulfides using stoichiometric amount of peroxides6
and hypervalent iodine reagents7 with the assistance of various
transition-metal-catalysts such as iron,8 vanadium,9 copper,10
25 titanium,11 cobalt,12 magnesium,13 silver14 and zinc15 salts.
Unfortunately, most of these methods involve the use of some
toxic metal reagents, and hazardous oxidants or complex reaction
procedures, which led to the generation of a large volume of
wastes. Another problematic scenario pertaining to traditional
30 methods is that most of them are usually accompanied by over
oxidation of sulfoxide to the sulfone. Recently, the metal-free
reactions of alkenes and thiols under dioxygen leading to β-oxy
sulfoxides and β-keto sulfoxides were independently reported by
Yadav16 and Lei,17 in which the co-oxidation of the olefin carbon
35 to form C-O or C=O bond occurred concurrently. In 2016,
Klussmann and co-workers reported a methanesulfonic acid
(MsOH)-catalyzed selective sulfoxidation of alkenes with thiols
for the construction of sulfoxides in the presence of tert-butyl
hydroperoxide.18 Very recently, Chi et al. also presented a one-
40 pot selective synthesis of sulfoxides from alkenes and thiols using
N-fluorobenzenesulfonimide (NFSI) as a radical initiator
functionalization
of
organic
molecules
has recently
attracted significant interests from the synthetic community.22 As
a part of our continued studies focusing on the synthesis of
70 sulfur-containing compounds,23 herein, we wish to report a facile
and efficient visible-light-induced method for the selective
construction of sulfoxides via Rose Bengal-catalyzed
sulfoxidation of alkenes with thiols using molecular oxygen (air)
as the oxidant and oxygen source (eqn (1)).
R2
O
S
R2
ose en a
l 5
mo
l
%
R
B
g
+
(
)
R3
1
( )
H
S
R1
R3
.
,
,
R1
r
Et H H
O / 2O
t 2h
a r
i
O
( )
2
75
Initially, we started the investigation of visible-light-induced
sulfoxidation reaction using styrene 1a and 4-methylbenzenethiol
2a as the model substrates in the presence of Eosin Y (5 mol %).
The model reaction was carried out by exposure to air in
80 CH3CN/H2O (v/v = 1/1) under irradiation with 3 white LED
lamps. To our delight, the desired product 3a was obtained in
15% yield after 2 h (Table 1, entry 1). Inspired by this result, a
series of metal-free photocatalysts such as Na2-eosin Y, Eosin B,
Rose Bengal, Rhodamine B, and Acridine Red were investigated
85 (Table 1, entry 2-6). Among the above photocatalysts tested,
Rose Bengal was demonstrated the highest catalytic activity
leading to the desired product 3a in 53% yield (Table 1, entry 4).
a
Institute of Medicine and Material Applied Technologies, Key
Laboratory of Pharmaceutical Intermediates and Analysis of Natural
Medicine, School of Chemistry and Chemical Engineering, Qufu Normal
45 University,
Qufu
273165,
Shandong, China.
E-mail:
weiweiqfnu@163.com; huawang_qfnu@126.com
† Electronic Supplementary Information (ESI) available: Experimental
details. See DOI: 10.1039/b000000x/
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Green Chemistry
Page 2 of 5
Table 2 Results for visible-light inditated sulfoxidation of alkenes with
Table 1 Optimization of the reaction conditions
25 thiols leading to sulfoxides ab
O
S
o oca a s ca a
s
Ph t
t ly t t ly t
R2
ose en a
mo
l
R
B
l
5
g
%
)
(
w
e
R2
O
S
3W hit LED
+
w
e
SH
3W hit LED
,
,
,
so ven
l
r
R3
H
S
t
t 2h
+
R1
,
,
r
Et H H
t 2h
O / 2O
r
Ai
R1
R3
O
( )
2
a
3
a
1
a
2
1
r
Ai
2
3
O
( )
2
ruc ures o
t
o oca a s s:
St
f Ph
t
t
ly
t
O
O
S
O
S
S
a
a
COOH
COON
COON
r
r
B
r
r
B
B
O2N
a
NO2
B
c
a
3
72
%
)
3
3b 72
89%
%
(
(
)
(
)
a
HO
O
O
N
O
O
n
O
N
O
O
O
O
S
O
S
O
S
r
B
r
B
r
r
B
r
r
B
B
B
-
os n
i
a
os n
E
Y
N
2 E
i
Y
os
E i
B
Cl
F
e
M
O
Cl
3d 71
%
e
3
(
)
3f
5
3%
(
55
%
( )
)
Cl
Cl
Cl
O
S
O
O
S
COOH
S
a
COON
I
I
Cl
N
O
N
O2N
Cl
H
. .
.
,
=
HCl
r
:
N
O
N
3g
3i
1
)
6
1
%
(
60%
(
d
0 98
3
h
4
0%
)
(
)
a
N
O
O
O
O
S
I
R
I
O
S
O
S
cr ne
idi
e
R
d
ose en
a
l
o am ne
d
Rh i B
A
B
g
N
Entry Photocatalyst (mol%) Solvent
Yield (%)b
3l
1
8%
3k
1
6%
(
)
3
90%
(
)
j
(
)
1
2
3
4
5
6
7
8
Eosin Y (5)
Na2-eosin Y (5)
Eosin B (5)
CH3CN/H2O (1:1)
CH3CN/H2O (1:1)
CH3CN/H2O (1:1)
CH3CN/H2O (1:1)
CH3CN/H2O (1:1)
CH3CN/H2O (1:1)
DME/H2O (1:1)
EtOH/H2O (1:1)
THF/H2O (1:1)
DCE/H2O (1:1)
Toluene/H2O (1:1)
1,4-dioxane/H2O (1:1) 21
Acetone/H2O (1:1)
EtOH/H2O (2:1)
EtOH
15
36
26
53
16
14
35
89
7
O
S
O
S
O
O
S
O
OCH3
Rose Bengal (5)
Rhodamine B (5)
Acridine Red (5)
Rose Bengal (5)
Rose Bengal (5)
Rose Bengal (5)
Rose Bengal (5)
Rose Bengal (5)
Rose Bengal (5)
Rose Bengal (5)
Rose Bengal (5)
RoseBengal (5)
RoseBengal (5)
RoseBengal (1)
RoseBengal (2)
RoseBengal (10)
Rose Bengal (5)
Rose Bengal (5)
RoseBengal (5)
--
o
n
3
3
68
%
)
(
m
60%
(
3
4
)
3%
(
)
O
S
O
S
O
S
F
3p
5
%
r
3
6
(
)
3q 63
5
(
6%
)
%
(
)
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
45
17
O
S
O
S
O
S
OCH3
OCH3
Cl
u
3
90%
3t
1
%
s
3
6
(
)
20
69
32
46
17
23
71
%
(
)
(
)
O
S
O
S
O
S
H2O
w
x
3
75
%
)
v
3
3
82
%
)
(
EtOH-H2O (1:1)
EtOH-H2O (1:1)
EtOH-H2O (1:1)
EtOH-H2O (1:1)
EtOH-H2O (1:1)
EtOH-H2O (1:1)
EtOH-H2O (1:1)
8
4
%
(
(
)
O
O
S
84
S
S
67c
62d
0e
c
)
z
3y
60%
3
2
9%
(
)
(
a
trace
Reaction conditions: 1 (0.2 mmol), 2 (0.3 mmol), Rose Bengal (5.0
b
mol%), EtOH-H2O (2 mL, v1/v2=1:1), 3W white LED lamps, rt, air, 2h.
a Reaction conditions: 1a (0.2 mmol), 2a (0.3 mmol), photocatalyst (1-10
5 mol %), solvent 2 ml), 3W white LED lamps, rt, air, 2h. DME: 1,2-
30 Isolated yields based on 1. c phenylacetylene was used (0.2 mmol).
b
dimethoxyethane; DCE: 1,2-dichloroethane; THF: tetrahydrofuran;
with thiols (Table 2). Gratifyingly, both electron donating and
electron-withdrawing aromatic substituents were tolerated in the
terminal alkenes, and the reaction worked well with the styrene
bearing electron donating groups (3a-3h). It should be noted that
Isolated yields based on 1a. c 3W blue LED lamps. 3W green LED
d
lamps. e Without visible-light irradiation.
Further optimization of solvents found that the reaction
10 performed in EtOH/H2O (v:v = 1/1) gave the best yield (89%) of
3a (Table 1, entries 7-16). Notably, this visible-light-induced
sulfoxidation reaction also proceeded smoothly in water (Table 1,
entry 16). The increase or reduction of the amount of photoredox
catalysts did not improve the reaction efficiencies (Table 1,
15 entries 17-19). In addition, the desired product was also obtained
in 67% and 62% yields when the reaction was conducted under
irradiation with 3 W blue and green LED lamps (Table 1, entries
20 and 21). It should be noted that this sulfoxidation reaction did
not occur in the absence of visible-light irradiation and only a
20 trace amount of product was detected without photocatalyst
(Table 1, entries 22 and 23).
35
a range of functional groups such as methoxy, halogen,
chloromethyl and nitro groups were compatible with this reaction,
and the corresponding products could be used for further
transformation. The reaction of more sterically demanding α-
methylstyrene with 4-methylbenzenethiol proceeded smoothly to
40 produce the desired product 3i in 60% yield. Notably, heterocycle
aromatic alkene such as 2-vinylpyridine could also work well in
this reaction to give the expected product 3j in 90% yield.
Nevertheless, the corresponding products (3k-3m) were obtained
in relatively low yields when aliphatic alkenes such as
45 cyclopentene, hex-1-ene, and methyl acrylate were used as the
substrates. The scope of this sulfoxidation reaction was further
expanded to a series of thiols. In general, aryl thiols bearing
electron-rich or -poor groups on the aryl rings were all suitable
With the optimized conditions in hand, we then examined the
generality of this visible-light initiated sulfoxidation of alkenes
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DOI: 10.1039/C7GC01416C
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Green Chemistry
substrates leading to the corresponding products in moderate to
key intermediate in the present reaction system (eqn (7)).
good yields (3n−3t). It was found that various aliphatic thiols
with the long aliphatic chains were also well compatible with the
reactions to deliver the corresponding products 3u-3x in good
yields. To our delight, heterocycle alkylthiol such as thiophen-2-
ylmethanethiol could also be employed in this transformation to
40
Moreover, an on/off visible light irradiation experiment was
carried out to verify the effect of photo irradiation, and showing
that the continuous irradiation of visible light is necessary for
promoting the present transformation (Figure 1). In addition,
fluorescence quenching experiments were also investigated to
5
give the product 3y in 60% yield. In addition, when aromatic 45 prove an energy transfer process between thiol 2a and Rose
alkyne such as phenylacetylene was tested in the present reaction
system, the corresponding vinylsulfoxide product 3z was
10 obtained in 29% yield. Nevertheless, only a trace amount of
product was detected when aliphatic alkyne such as hex-1-yne
was employed in this reaction system.
Bengal (Stern-Volmer studies) (see Figures 2 and 3). Indeed, it
was found that the emission intensity of excited Rose Bengal
(RB*) was dramatically diminished along with the increasing of
the amount of thiol 2a. On the contrary, none of such effect was
50 observed when styrene 1a was added separately (see ESI†).
A series of control experiments were further carried out to
better understand the possible mechanism of this transformation.
15 As shown in eqn (2), when TEMPO (2,2,6,6-tetramethyl-1-
piperidinyloxy, a well-known radical scavenger) was added in the
model reaction system, the reaction was extremely inhibited and
only a trace amount of product 3a was detected, suggesting that a
radical process might be involved in the present reaction.
20 Moreover, only a trace amount of product 3a was detected when
the model reaction was conducted under nitrogen atmosphere
(eqn (3)). Also, 18O-labeling experiment was performed to
determine the source of oxygen in sulfoxide. When the reaction
of 1a and 2a was conducted in the presence of EtOH/H2O18 under
25 air, the corresponding product 3a was isolated in 80% yield and
none of O18-3a was detected (eqn (4)). These results indicate that
air (O2) is essential for this reaction and the oxygen atom of
sulfoxide came from dioxygen (air). Furthermore, none of the
desired product was detected when the reaction of styrene 1a with
30 1,2-diphenyldisulfane was carried out under standard conditions,
which showed the disulfide might not be involved in this
transformation (eqn (5)). In addition, when the model reaction
was carried out for 20 min, the desired product 3a was obtained
in 14% yield along with the formation of sulfide 7a in 74% yield
35 (eqn (6)). Furthermore, when the preformed sulfide 7a was added
separately under the standard conditions, the desired product 3a
was obtained in 77% yield, suggesting that sulfide might be the
Figure 1. Visible light irradiation on/off experiment
ose en a
l 5
mo
l
%
)
O
S
R
B
g
(
Figure 2 Quenching of Rose Bengal fluorescence emission in the
55 presence of thiol 2a.
v
w
e
h
3W hit LED
(
)
Ph
H
S
2
( )
.
Ph
,
,
,
a r
i 2h
r
Et H H
/ 2O
t
O
a
r
ace
a
1
3
t
(
a
2
e
u v
q i
)
TEMP
2
(
O
)
1.20
1.16
1.12
1.08
1.04
1.00
0.96
ose en a
l 5
mo
l
%
R
B
O
S
g
(
)
v
w
e
h
3W hit LED
(
O
)
Ph
H
S
. .
3
,
Ph
( )
r
Et H H
2O
t 2h
/
N2
a
a
r
ace
t
(
a
1
3
2
)
ose en a
mo
l
%
R
B
l 5
(
O
S
g
)
v
h
w
e
3W hit LED
(
)
Ph
Ph
H
S
. .
4
( )
,
Et H H O18 t 2h
r
O
/
a r2
a
a
2
a
3
80%
(
i
1
O
(
)
2
)
O
S
ose en a
l 5
mo
l
%
R
h
B
g
0
2
4
6
8
10
12
-6
14
16
18
20
(
)
v
w
e
3W hit LED
Ph
S
+
(
)
C
X10 mol/L
5
Ph
[thiophenol]
Ph
( )
Ph
S
.
,
,
,
a r
r
Et H H
O
t
i 2h
/
2O
a
1
3k
0%
)
(
Figure 3. Stern-volmer plots.
O
S
ose en a
mo
l
%
)
)
Ph
R
h
B
l 5
(
e
g
S
v
w
On the basis of the above results and referring to previous
literatures,24,25 a possible reaction pathway was thus proposed as
60 shown in Scheme 1. Initially, Rose Bengal was converted to the
excited RB* under the visible-light irradiation. Then, a single
electron transfer from thiol 2 to RB* afforded the radical cation 4
and RB•− radical anion. The oxidation of RB•− by dioxygen (air)
3W hit LED
(
Ph
+
6
( )
a
a
1
2
. .
,
r
a r
i
Et H H
t
O
/
2O
a
3
a
7
14
%
( )
74
(
%
)
m n
20
i
O
ose en a
l 5
mo
l
%
R
B
g
(
)
S
S
v
w
e
3W hit LED
)
h
Ph
(
Ph
7
( )
.
,
,
,
a r
r
Et H H
2O
t
i 2h
O
/
a
3
a
77
(
%
7
)
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Green Chemistry
Page 4 of 5
generated the ground state Rose Bengal and O2•−. Subsequently,
the radical cation 4 is deprotonated by O2 leading to the
2002, 2, 17.
•−
45 4
5
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stabilized thiyl radical 5. Next, the addition of thiyl radical 5 to
alkene 1 would lead the formation of alkyl radical 6. Furthermore,
a hydrogen atom transfer (HAT) process underwent between thiol
2 and alkyl radical 6 to give sulfide intermediate 7 along with the
regeneration of the thiyl radical 5. Finally, the sensitized
photooxidation of sulfide 7 with dioxygen produced the desired
sulfoxide 3.25
5
6
50
7
8
55
H
O2
O2
-
R3
2
H
S
R3
H
S
R3
S
5
R2
4
9
*
*
R1
RB
RB
1
O2
60
v
h
S
R1
R3
RB
R2
6
O2
R3-
H
S
2
10 (a) R. Liu, L.-Z. Wu, X.-M. Feng, Z. Zhang, Y.-Z. Li, Z.-L.
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13 M.-Y. Chen, L. N. Patkar and C.-C. Lin, J. Org. Chem., 2004,
69, 2884.
HAT
R3
65
70
S
4
O
H
R2
O
S
R2
O
O2
7
S
R1
R3
S
R3
R1
R3
R2
R1
2
+
7
8
e
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75 14 R. Das and D. Chakraborty, Synthesis, 2011, 277.
15 X-F. Wu, Tetrahedron Lett., 2012, 53, 4328.
Scheme 1. Postulated reaction pathway
16 T. Keshari, V. K. Yadav, V. P. Srivastava and L. D. S. Yadav,
Green Chem., 2014, 16, 3986.
17 H. Wang, Q. Lu, C. Qian, C. Liu, W. Liu, K. Chen and A. Lei,
In summary, a rapid and facile approach to the visible-light
induced selective sulfoxidation reaction of alkenes with thiols has
been developed using air as the environmentally-benign oxidant.
80
85
Angew. Chem., Int. Ed., 2016, 55, 1094.
18 H-L. Yue, and M. Klussmann, Synlett, 2016, 27, 2505.
19 Y. Zhang, Z. R. Wong, X. Wu, S. J. Lauw, X. Huang, R. D.
Webster and Y. R. Chi, Chem. Commun., 2017, 53, 184.
15
A series of biologically important sulfoxides could be
conveniently and efficiently prepared in moderate to good yields
using of simple and readily available materials. The present
method is of great value from both green chemistry and organic
synthesis perspectives because of its desirable features including
20 operation simplicity, high atom efficiency, eco-energy source,
green solvent, metal-free catalysis and ambient conditions. The
application of this powerful system to the synthesis of other
sulfur-containing compounds is currently underway in our
laboratory.
20 Selective examples: (a) D. A. Nicewicz and D. W. C.
MacMillan, Science, 2008, 322, 77; (b) C. K. Prier, D. A.
Rankic and D. W. C. MacMillan, Chem. Rev., 2013, 113, 5322;
(c) J. M. R. Narayanam and C. R. J. Stephenson, Chem. Soc.
Rev., 2011, 40, 102; (d) T. P. Yoon, M. A. Ischay and J. Du, Nat.
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Blum and T. P. Yoon, Chem. Rev., 2016, 116, 10035; (k) N. A.
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21 D. Yang, B. Huang, W. Wei, J. Li, G. Lin, Y. Liu, J. Ding, P.
Sun and H. Wang, Green Chem., 2016, 18, 5630.
90
25
This work was supported by the National Natural Science
Foundation of China (No. 21302109, 21302110, 21375075, and
21675099), the Natural Science Foundation of Shandong
Province (ZR2015JL004 and ZR2016JL012), and the Taishan
30 Scholar Foundation of Shandong Province.
95
22 (a) D. Ravelli, M. Fagnoni and A. Albini, Chem. Soc. Rev.,
2013, 42, 97; (b) Q. Shi, P. Li, X. Zhu and L. Wang, Green
Chem., 2016, 18, 4916; (c) L. Zhang, H. Yi, J. Wang and A. Lei,
Green Chem., 2016, 18, 5122; (d) A. A. Ghogare and A. Greer,
Chem. Rev. 2016, 116, 9994; (e) P. K. Shyam and H-Y. Jang, J.
Org. Chem. 2017, 82, 1761.
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