Visible-Light-Induced Hydroxysulfurization and Alkoxysulfurization of Styrenes in the Absence of Photocatalyst: Synthesis of β-Hydroxysulfides and β-Alkoxysulfides

Article abstract of DOI:10.1002/adsc.201900140

We developed hydroxysulfurization and alkoxysulfurization of styrenes using a visible-light synthetic strategy in the absence of photocatalyst and oxidant. This strategy provided the corresponding β-hydroxysulfides and β-alkoxysulfides in moderate to good yields with high regioselectivity. The reaction was tolerated by a wide range of functional groups. This is the first example of ArSSAr/CBr₄ system has been introduced into organic transformation. (Figure presented.).

Full text of DOI:10.1002/adsc.201900140

Title: Visible-Light-Induced Hydroxysulfurization and
Alkoxysulfurization of Styrenes in the Absence of Photocatalyst:
Synthesis of β-Hydroxysulfides and β-Alkoxysulfides
Authors: Hongjie Ruan, Ling-Guo Meng, Lingqiong Zhu, and Lei Wang
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
published online in Early View as soon as possible and may be different
to this Accepted Article as a result of editing. Readers should obtain
the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: Adv. Synth. Catal. 10.1002/adsc.201900140
Link to VoR: http://dx.doi.org/10.1002/adsc.201900140

10.1002/adsc.201900140
Advanced Synthesis & Catalysis
UPDATE
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Visible-Light-Induced Hydroxysulfurization and
Alkoxysulfurization of Styrenes in the Absence of Photocatalyst:
Synthesis of β-Hydroxysulfides and β-Alkoxysulfides
Hongjie Ruan,a Ling-Guo Meng,a,* Lingqiong Zhu,a and Lei Wanga,b*
a
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R.
b
China
Corresponding author: phone: +86-561-380-2069, fax number: +86-561-309-0518, E-mail: milig@126.com,
leiwang@chnu.edu.cn
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
could not occur without electrolysis auxiliary
conditions,[6a] peroxide reagents,[6b-c] a strong base,[6d]
Abstract: We developed hydroxysulfurization and
alkoxysulfurization of styrenes using a visible-light
synthetic strategy in the absence of photocatalyst and
oxidant. This strategy provided the corresponding β-
hydroxysulfides and β-alkoxysulfides in moderate to
good yields with high regioselectivity. The reaction was
tolerated by a wide range of functional groups. This is
the first example of ArSSAr/CBr4 system has been
introduced into organic transformation.
or
a
transitional metal,[6e] (Scheme 1a–1e).
Accordingly, the ability to find simple and green
methods to accomplish such difunctionalization of
alkenes to prepare β-oxy sulfides holds scientific
merit.
Visible-light-induced organic transformations
recently receipted prominent attention from chemist
because of a demonstrable effect on the development
of organic synthesis. Many photocatalyzed organic
reactions, including unexpected synthetic reactions,
have been accomplished through these synthetic
platforms.[7] Photoinitiated difunctionalizations of
carbon-carbon multiple bonds have been used
intensively to produce structurally diverse
molecules.[8] Research on the direct conversion of
different groups of combined alkenes cannot be
Keywords: visible-light; promoter; photosynthesis;
hydroxysulfurization; alkoxysulfurization
The ability to construct a simple and convenient
synthetic strategy for the formation of chemical
bonds is an onging research priority. The
difunctionalization mode is an attractive and efficient
method to introduce two functional groups into an
unsaturated hydrocarbon, producing complicated
molecules in one step.[1] Among reported
difunctionalization reactions, the direct addition of
thiol to carbon-carbon double bond has been
investigated extensively for the preparation of
accomplished without organic dyes or transition-
[9]
metal complexes as photosensitizers.
practical visible-light-promoted
To identify
difunctional
transformations in the absence of photocatalyst
presents a significant challenge.
organic
sulfur
compounds
under
catalytic
Disulfides, as versatile synthetic precursors, have
conditions.[2] β-Oxy sulfides, as one of the familiar
class organic molecules, are widely used as important
synthetic precursors for the synthesis of organic
functional compounds.[3] This unit also is found in
pharmaceutical and natural compounds with
been applied to
a
variety of photochemical
reactions,[10] but only a few studies have been
reported about photo-driven difunctionalization
biological
activity.[4]
Introduced
separately,
traditional obtaining β-oxy sulfides resulted from the
reaction of epoxides and thiols or disulfides; however,
poor regioselectivity or chemoselectivity usually was
observed.[5] Alternatively, β-oxy sulfides also could
be formed through hydroxysulfurization or
alkoxysulfurization of alkenes. These bis-
functionalization modes have shown synthetic
convenience and efficiency due to the availability of
Scheme 1. Selected examples for the synthesis of β-oxy sulfides
from alkenes.
starting
materials
without
the
required
preformations.[6] These transformations, however,
1
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900140
Advanced Synthesis & Catalysis
Table 1. Optimization of the reaction conditions.a)
Entry
Light source
Solvent
Yieldb) (%)
Blue LED (420–470 nm)
—
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
Acetone
DCE
THF
DMF
EtOAc
Toluene
CH3CN
H2O
66
NRc)
76d)
86
NRc)
NRc)
NRc)
40d)
42e)
82
79
76
68
68
66
61
52
54
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
Blue LED (420–425 nm)
Blue LED (450–455 nm)
Red LED (610–650 nm)
Green LED (480–570 nm)
Yellow LED (570–610 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
Blue LED (450–455 nm)
—
a)
Reaction conditions: 1a (0.60 mmol), 2a (0.20 mmol), CBr4
(0.20 mmol), H2O (1.0 mmol), light source, N2, solvent (4.0 mL),
b)
c)
d)
r.t., 12 h. Isolated yield. NR = no reaction. CBr4 (0.10
mmol) was added. e) PhSSPh (0.10 mmol) was added.
Scheme 2. Visible-light induced hydroxysulfurization of alkenes
[Reaction conditions: 1 (0.60 mmol), 2 (0.20 mmol), CBr4 (0.20
mmol), H2O (1.0 mmol), blue LED (450–455 nm), N2, CH2Cl2
(4.0 mL), r.t., 12 h; isolated yield of the product.]
without
a
photocatalyst, particularly when
introducing different groups into carbon-carbon
double bonds in one step, has not yet been
addressed.[11] In our recent studies on phototriggered
transformation with photocatalyst-free conditions,[12]
we attempted to further examine the possibility of a
reaction between disulfides and styrenes; however,
we did not observe a reaction under nitrogen (N2)
with blue light-emitting diode (LED) irradiation.
Conversely, we improved the efficiency of this
difunctionalization reaction when we added carbon
tetrabromide (CBr4) to the reaction. Note that we
accomplished this reaction without a photocatalyst or
a strong oxidant. Meanwhile, ArSSAr/CBr4 reaction
system was first used as a universal platform for
hydroxysulfurization and alkoxysulfurization of
styrenes; however, no literature has reported the use
of diol as a substrate for the preparation of β-
alkoxysulfide (Scheme 1f). [13] In this study, we report
this photochemical difunctionalization for the
preparation of β-oxy sulfides in the absence of a
photocatalyst and an oxidant. This greener
hydroxysulfurization and alkoxysulfurization of
styrenes has shown high efficiency and
regioselectivity.
presence of 5.0 equiv. of water (H2O) and 1.0 equiv.
of CBr4, we obtained the desired product 1-phenyl-2-
(phenylthio)ethan-1-ol (3aa) in 66% yield (Table 1,
entry 1). No any reaction occurred when the reaction
was performed in the absence of a light source (Table
1, entry 2). Because of these effective results, we then
tested different light sources, including fixed
wavelength of blue LED (420–425 and 450–455 nm),
red LED (610–650 nm), green LED (480–570 nm),
and yellow LED (570–610 nm). Among these light
sources, we found blue LED (450–455 nm) to be the
best (Table 1, entries 3–7). The yield of 3aa declined
with a reduced amount of CBr4 and PhSSPh (Table 1,
entries 8 and 9). Further solvent screening indicated
that acetone, DCE, and THF gave comparable
product yields (Table 1, entries 10–12). Additionally,
we obtained moderate yields (52–68%) when we used
dimethylformamide (DMF), ethyl acetate (EtOAc),
toluene, and H2O as the reaction media (Table 1,
entries 13–17). Notably, we also produced the desired
product 3aa under solvent-free conditions, albeit with
a moderate yield (Table 1, entry 18).
With these optimized reaction conditions, we first
studied the substrate scope of the reaction; the results
are shown in Scheme 2. As for the para-substituents
on the phenyl rings of aromatic alkenes, substrates
1b–1f with either electron-rich or electron-poor
groups could react with disulfide 2a to give the
corresponding products 3ba–3fa in 70–83% yields;
we obtained moderate yield of 3ga when we used p-
trifluoromethylstyrene in the reaction. Furthermore,
We began our study with the model reaction of
styrene (1a) and diphenyl disulfide (2a) for the
optimization of reaction conditions. When the model
reaction was conducted in dichloromethane (CH2Cl2)
under blue LED (420–470 nm) irradiation in the
2
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900140
Advanced Synthesis & Catalysis
Scheme 3. Visible-light induced alkoxysulfurization of alkenes
[Reaction conditions: 1 (0.60 mmol), 2 (0.20 mmol), CBr4 (0.20
mmol), HO(CH2)nOH (5.0 mmol), blue LED (450–455 nm),
CH2Cl2 (4.0 mL), rt, 12 h; isolated yield of the product.]
Scheme 4. Control experiments.
the interaction of the intermolecular hydroxyl groups.
For other aromatic alkenes containing different
with the substituents located on the meta-position of
the phenyl rings, we obtained the desired products
3ha–3ja in 50–72% yields. When we used o-fluoro-,
o-chloro-, and o-bromostyrene as substrates, 58–62%
yields of 3ka–3ma were obtained without obvious
steric effect. For dimethyl substituted olefins 1n and
1o, the corresponding products 3na and 3oa were
produced in 76% and 56% yields, respectively.
Directly linked and condensed diphenyl olefins (1p
and 1q) led to satisfactory yields. On the other hand,
we also examined a variety of disulfides under
optimal reaction conditions. The para-substituted
disulfides 2b–2g all transformed into the desired
products 3ab–3ag with 71–86% yields. The
disulfides containing electron-donating groups
afforded slightly higher yields than that of disulfides
bearing electron-withdrawing groups. Meanwhile, the
disulfides with a substituted group (Me, Cl, or Br) on
the meta-position of the phenyl rings reacted with 1a
to produce the corresponding products 3ah–3aj in
58–78% yields. When a halogen atom existed in the
ortho-position of the benzene rings in substrates 2,
the corresponding products 3ak–3am were afforded
in 75–85% yields. Note that we did not observe any
of the desired products when we used aliphatic alkene
or aliphatic disulfide as one of the substrates.
We attempted the possibility of difunctionalization
reaction of alkenes from hydroxysulfurization to
alkoxysulfurization by using diol in place of H2O; the
results are shown in Scheme 3. When diols with
different lengths of carbon chain, including
ethanediol, propanediol, butanediol, and pentanediol,
reacted with styrene (1a) and diphenyl disulfide (2a)
under standard conditions, the corresponding
alkoxysulfurization products (4aa, 4aaIII–4aaV)
were produced in 44–69% yields. The efficiency of
the reaction was sensitive to the distance between
hydroxyl groups in diols, which could be attributed to
t
substituted groups (Me, Bu, Cl, and Ph) in the para-
or meta-position of the phenyl rings, the reactions
also proceeded smoothly to produce the desired
products (4ba, 4ca, 4ea, 4ha, 4pa) in moderate to
good yields. Furthermore, disulfides bearing MeO,
and Me groups on the phenyl rings afforded the
products 4ab and 4ac in 73% and 71% yields,
respectively. Nevertheless, the reaction of ethanol
with 1a and 2a failed.
It should be noted that when hydroxysulfurization
and alkoxysulfurization of styrene was performed in a
5 mmol scale, 62% and 40% yields of 3aa and 4aa
were isolated, respectively. Conversely, no reaction
was occurred when PhSeSePh or PhTeTePh was in
place of PhSSPh. The reactions were complicated
when PhCOOH and CH3COOH was used as
expanded oxy-nucleophiles.[14]
To elaborate on the possible reaction mechanism,
we performed the control experiments, as depicted in
Scheme 4. The difunctionalization was nearly
inhibited when TEMPO (2,2,6,6-tetramethyl-1-
piperidinyloxy) was added to the reaction, which
suggested that a free radical process was involved in
the reaction (Scheme 4a). Conversely, an obvious
reaction was not observed in the absence of CBr4
(Scheme 4b). Furthermore, a cross-coupling product
1-(4-methoxyphenyl)-2-phenyldisulfane 5 in 54%
yield was isolated when the reaction of disulfide 2a
and 2b was irradiated with blue LED in N2 (Scheme
4c), and the cross-coupling reaction was interrupted
as TEMPO was added to the reaction (Scheme 4d).
Furthermore, the thiyl radical could be detected by
HRMS analysis (Scheme 4e, see SI for detail) and no
reaction was found when PhSSPh was removed from
the reaction (Scheme 4f). These results suggested that
S–S bond homolytic cleavage in disulfides
experienced the reaction smoothly under visible-light
3
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900140
Advanced Synthesis & Catalysis
mmol) or diol (5.0 mmol) and carbon tetrabromide (0.20
mmol) was added. The reaction mixture was stirred under
blue LED (450–455 nm) irradiation for 12 h at room
temperature. The residue was then purified by column
chromatography on silica gel (petroleum ether/CH2Cl2 =
1:4) to give the desired product.
irradiation
and
subsequently
drove
the
difunctionalizations of aromatic alkenes.
Acknowledgements
We gratefully acknowledge the National Natural Science
Foundation of China (21772062, 21572078, 21402061),
the Young Talent Key Project of Anhui Province
(gxyqZD2016411), and the Natural Science Foundation of
Anhui (No. 1708085MB45) and the Scientific Research
Project of Anhui Provincial Education Department
(KJ2015TD002) for financial support of this work.
Scheme 5. Possible mechanism.
On the basis of the results of control experiments
and relevant reports, a plausible mechanism is
proposed, shown in Scheme 5. Initially, a homolytic
cleavage of disulfide 2a underwent a reaction to
generate thiyl radical A under the irradiation of blue
LED (450–455 nm). The formed A might react with
CBr4 to give a tribromomethyl radical B, which then
abstracted hydrogen from H2O or HOCH2CH2OH to
afford a corresponding hydroxyl radical (•OH) or
alkoxyl radical (•OCH2CH2OH). The possible
References
[1] a) G. Yin, X. Mu, G. Liu, Acc. Chem. Res. 2016, 49,
2413–2423. b) A. Minatti, K. Muñiz, Chem. Soc. Rev.
2007, 36, 1142–1152. c) C. J. R. Bataille, T. J. Donohoe,
Chem. Soc. Rev. 2011, 40, 114–128.
•
existence of OH and bromoform (CHBr3) could be
proven by electron spin resonance (ESR) and gas
chromatography mass spectrometry (GC-MS)
analysis (see SI for detail), respectively. Notably,
however, the fated interaction of A with CBr4
remained unclear. Conversely, the addition of A to
[2] a) T. Kondo, S. Uenoyama, K. Fujita, T. Mitsudo, J.
Am. Chem. Soc. 1999, 121, 482–483. b) N. Taniguchi, J.
Org. Chem. 2006, 71, 7874–7876. c) D. Wang, Z. Yan, Q.
Xie, R. Zhang, S. Lin, Y. Wang, Org. Biomol. Chem. 2017,
15, 1998–2002. d) A. A. Vieira, J. B. Azeredo, M. Godoi,
C. Santi, E. N. S. Júnior, A. L. Braga, J. Org. Chem. 2015,
80, 2120–2127. e) H. Cui, X. Liu, W. Wei, D. Yang, C. He,
T. Zhang, H. Wang, J. Org. Chem. 2016, 81, 2252–2260.
f) K. Sun, Y. Lv, Z. Shi, S. Mu, C. Li, X. Wang, Org.
Biomol. Chem. 2017, 18, 5258–5262. g) H. Wang, G.
Wang, Q. Lu, C.-W. Chiang, P. Peng, J. Zhou, A. Lei,
Chem. Eur. J. 2016, 22, 14489–14493.
styrene 1a underwent
a
reaction to afford
intermediate C. The coupling product D might be
formed by GC-MS analysis (see SI for detail), which
indirectly caused this reaction between A and 1a.
Finally, intermediate C coupled with •OH or
•OCH2CH2OH to give the desired products 3aa or
4aa. Note that the concomitant PhSBr during the
generation of B could not react with H2O or
HOCH2CH2OH to generate the desired products 3aa
or 4aa.
[3] a) J. R. Luly, N. Yi, J. Soderquist, H. Stein, J. Cohen, T.
J. Perun, J. J. Plattner, J. Med. Chem. 1987, 30, 1609–1616.
b) C. Alvarez-Ibarra, R. Cuervo-Rodrìguez, M. C.
Fernìnedz-Monreal, M. P. Ruiz, J. Org. Chem. 1994, 59,
7284–7291. c) H. Sugihara, H. Mabuchi, M. Hirata, T.
Iamamoto, Y. Kawamatsu, Chem. Pharm. Bull. 1987, 35,
1930–1952. d) M. A. Adger, J. B. Barkley, S. Bergeron, M.
W. Cappi, B. E. Flowerden, M. P. Jackson, R. McCange, T.
C. Nugent, S. M. Roberts, J. Chem. Soc., Perkin Trans 1
1997, 3501–3507.
In conclusion, we developed an efficient green
photosynthetic strategy for the hydroxysulfurization
and alkoxysulfurization of styrenes under catalyst-
free and oxidant-free conditions. A variety of β-
hydroxysulfides and β-alkoxysulfide were obtained in
good yields with high regioselectivity. Not only did
the reaction provide an alternative pathway to
desired products, but also this is the first use of
ArSSAr/CBr4 system for the generation of β-
hydroxysulfides and β-alkoxysulfides.
[4] a) S. W. Kaldor, V. J. Kalish, J. F. Davies II, B. V.
Shetty, J. E. Fritz, K. Appelt, J. A. Burgess, K. M.
Campanale, N. Y. Chirgadze, D. K. Clawson, B. A.
Dressman, S. D. Hatch, D. A. Khalil, M. B. Kosa, P. P.
Lubbehusen, M. A. Muesing, A. K. Patick, S. H. Reich, K.
S. Su, J. H. Tatlock, J. Med. Chem. 1997, 40, 3979–3985.
b) E. J. Corey, D. A. Clark, G. Goto, A. Marfat, C.
Mioskowski, B. Samuelsson, S. Hammarstrom, J. Am.
Chem. Soc. 1980, 102, 1436–1439. c) E. J. Corey, D. H.
Hua, B.-C. Pan, S. P. Seitz, J. Am. Chem. Soc. 1982, 104,
6818–6820.
Experimental Section
General procedure for the visible-light induced
hydroxysulfurization and alkoxysulfurization of
styrenes: To a solution of aromatic alkene (0.60 mmol) in
4.0 mL of dichloromethane was added disulfide (0.20
mmol) under nitrogen atmosphere, and then water (1.0
4
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900140
Advanced Synthesis & Catalysis
[5] For selected examples for the synthesis of β-oxy
sulfides from epoxides, see: a) F. Fringuelli, F. Pizzo, S.
Tortoioli, L. Vaccaro, Adv. Synth. Catal. 2002, 344, 379–
384. b) S. R. Lanke, B. H. Bhanage, Catal. Commun. 2013,
41, 29–33. c) J. Dowsland, F. McKerlie, D. J. Procter,
Tetrahedron Lett. 2000, 41, 4923–4927. d) W. Guo, J.
Chen, D. Wu, J. Ding, F. Chen, H. Wu, Tetrahedron 2009,
65, 5240–5243. e) V. Ganesh, S. Chandrasekaran,
Synthesis 2009, 19, 3267–3278.
Chem. Commun. 2018, 54, 1976–1979. g) A. K. Yadav, L.
D. S. Yadav, Green Chem. 2015, 17, 3515–3520. h) G.
Bergonzini, C. Cassani, H. Lorimer-Olsson, J. Hörberg, C.-
J. Wallentin, Chem. Eur. J. 2016, 22, 3292–3295. i) B. Li,
D. Fan, C. Yang, W. Xia, Org. Biomol. Chem. 2016, 14,
5293–5297.
[9] a) K. Koike, M. Akita, Org. Chem. Front. 2016, 3,
1345–1349 and references cited therein. b) T. Courant, G.
Masson, J. Org. Chem. 2016, 81, 6945–6952 and
references cited therein. c) S. H. Oh, Y. R. Malpani, N. Ha,
[6] For selected examples for the synthesis of β-oxy
sulfides from alkenes, see: a) Y. Wang, L. Deng, H. Mei, B. Y.-S. Jung, S. B. Han, Org. Lett. 2014, 16, 1310–1313. d)
Du, J. Han, Y. Pan, Green Chem. 2018, 20, 3444–3449. b)
S.-F. Zhou, X. Pan, Z.-H. Zhou, A. Shoberu, J.-P. Zou, J.
Org, Chem. 2015, 80, 3682–3687. c) R. Zhang, S. Jin, Y.
Wan, S. Lin, Z. Yan, Tetrahedron Lett. 2018, 59, 841–847.
d) K. Choudhuri, A. Mandal, P. Mal, Chem. Commun.
2018, 54, 3759–3762. e) B. Movassagh, M. Navidi,
Tetrahedron Lett. 2008, 49, 6712. f) A. A. Vieira, J. G.
Azeredo, M. Godoi, C. Santi, E. N. Júnior, A. L. Braga, J.
Org. Chem. 2015, 80, 2120–2127. g) J. Yu, C. Gao, Z.
Song, H. Yang, H. Fu, Org. Biomol. Chem. 2015, 13,
4846–4850.
Y. Yasu, T. Koike, M. Akita, Org. Lett. 2013, 15, 2136–
2139. e) G. Ren, Z. Wu, L. Huan, C. Zhu, Adv. Synth.
Catal. 2017, 359, 3052–3056.
[10] a) F. Dénès, M. Pichowicz, G. Povie, P. Renaud,
Chem. Rev. 2014, 114, 2587–2693, and cited therein. b) Q.
Shi, P. Li, Y. Zhang, L. Wang, Org. Chem. Front. 2017, 4,
1322–1330. c) X. Xie, P. Li, Q. Shi, L. Wang, Org. Biomol.
Chem., 2017, 15, 7678–7684. d) X. Zhu, X. Xie, P. Li, J.
Guo, L. Wang, Org. Lett. 2016, 18, 1546–1549. e) L.-M.
Ye, L. Qian, Y.-Y. Chen, X.-J. Zhang, M. Yan, Org.
Biomol. Chem. 2017, 15, 550–554.
[7] For selected reviews, see: a) N. A. Romero, D. A.
Nicewicz, Chem. Rev. 2016, 116, 10075–10166. b) D.
Staveness, I. Bosque, C. R. J. Stephenson, Acc. Chem. Res.
2016, 49, 2295–2306. c) C. K. Prier, D. A. Rankic, D. W.
C. MacMillan, Chem. Rev. 2013, 113, 5322–5363. d) J.
Xuan, W.-J. Xiao, Angew. Chem., Int. Ed. 2012, 51, 6828–
6838.
[11] a) X. Baucherel, J. Uziel, S. Jugé, J. Org. Chem. 2001,
66, 4504–4510. b) A. Ogawa, H. Tanaka, H. Yokoyama, R.
Obayashi, K. Yokoyama, N. Sonoda, J. Org. Chem. 1992,
57, 111–115. c) A. Ogawa, R. Obayashi, H. Ine, N. Sonoda,
T. Hirao, J. Org. Chem. 1998, 63, 881–884.
[12] K. Ni, L.-G. Meng, K. Wang, L. Wang, Org. Lett.
2018, 20, 2245–2248.
[8] a) K. Nakafuku, S. C. Fosu, D. A. Nagib, J. Am. Chem.
Soc. 2018, 140, 11202–11205. b) J. Chen, Y. Cheng, J. Xie,
C. Zhu, Org. Lett. 2017, 19, 6452–6455. c) K. Wang, L.-G.
Meng, L. Wang, J. Org. Chem. 2016, 81, 7080–7087. d) A.
K. Yadav, L. D. S. Yadav, Green Chem. 2016, 18, 4240–
4244. e) R. Lin, H. Sun, C. Yang, W. Shen, W. Xia, Chem.
Commun. 2015, 51, 399–401. f) A. K. Yadav, K. N. Singh,
[13] E. S. Conner, K. E. Crocker, R. G. Fernando, F. R.
Fronczek, G. G. Stanley, J. R. Ragains, Org. Lett. 2013, 15,
5558–5561 and references cited therein.
[14] L. Sun, Y. Y. Yuan, M. Yao, H. Wang, D. Wang, M.
Gao, Y.-H. Chen, A. Lei, Org. Lett. 2019, 21, 1297–1300.
5
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900140
Advanced Synthesis & Catalysis
UPDATE
Visible-Light-Induced Hydroxysulfurization
and Alkoxysulfurization of Styrenes in the
Absence of Photocatalyst: Synthesis of β-
Hydroxysulfides and β-Alkoxysulfides
Adv. Synth. Catal. Year, Volume, Page – Page
Hongjie Ruan, Ling-Guo Meng* Lingqiong Zhu,
and Lei Wang*
6
This article is protected by copyright. All rights reserved.