Iodine-mediated synthesis of (E)-vinyl sulfones from sodium sulfinates and cinnamic acids in aqueous medium

Article abstract of DOI:10.1039/c5ra10896a

With water as the reaction medium, a green and efficient method has been developed for the synthesis of (E)-vinyl sulfones via I₂-mediated decarboxylative cross-coupling reactions of sodium sulfinates with cinnamic acids. This synthetic route could effectively avoid the use of toxic organic solvents and transition metal catalysts, and the target products could be obtained with moderate to excellent yields under green and mild conditions.

Full text of DOI:10.1039/c5ra10896a

View Article Online
View Journal
RSC Advances
This article can be cited before page numbers have been issued, to do this please use: J. Gao, J. Lai and
G. Yuan, RSC Adv., 2015, DOI: 10.1039/C5RA10896A.
This is an Accepted Manuscript, which has been through the
Royal Society of Chemistry peer review process and has been
accepted for publication.
Accepted Manuscripts are published online shortly after
acceptance, before technical editing, formatting and proof reading.
Using this free service, authors can make their results available
to the community, in citable form, before we publish the edited
article. This Accepted Manuscript will be replaced by the edited,
formatted and paginated article as soon as this is available.
You can find more information about Accepted Manuscripts in the
Information for Authors.
Please note that technical editing may introduce minor changes
to the text and/or graphics, which may alter content. The journal’s
standard Terms & Conditions and the Ethical guidelines still
apply. In no event shall the Royal Society of Chemistry be held
responsible for any errors or omissions in this Accepted Manuscript
or any consequences arising from the use of any information it
contains.
www.rsc.org/advances

RSC Advances
Page 1 of 5Jour nal Name
Dynamic Article Links ►
View Article Online
DOI: 10.1039/C5RA10896A
Cite this: DOI: 10.1039/c0xx00000x
www.rsc.org/xxxxxx
ARTI CLE TYPE
Iodine-mediated synthesis of (E)-vinyl sulfones from sodium sulfinates
and cinnamic acids in aqueous medium
Jian Gao, Junyi Lai and Gaoqing Yuan*
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
5
DOI: 10.1039/b000000x
† Electronic Supplementary Information (ESI) available: Detailed
experimental procedures, characterization of products, and NMR spectral
50 charts. See DOI: 10.1039/b000000x/
With water as the reaction medium, a green and
efficient method has been developed for the synthesis of
(E)-vinyl sulfones via I2-mediated decarboxylative
cross-coupling reactions of sodium sulfinates with
10 cinnamic acids. This synthetic route could effectively
avoid the use of toxic organic solvents and transition
metal catalysts, and the target products could be
obtained with moderate to excellent yields under green
and mild conditions.
15 Since 1960s, transition metal catalysts have increasingly
attracted one’s attention owing to their versatile reactivity and
practical applications in organic synthesis,1 especially for the
formation of carbonꢀcarbon and carbonꢀheteroatom bonds.2
Nevertheless, transitionꢀmetalꢀcatalyzed coupling reactions
20 have long been plagued by instinctive drawbacks of the
catalytic systems, such as expensive, toxic catalysts and
ligands, extra additives or coꢀcatalysts, harsh reaction
conditions and so on.3 So chemists desire to look for greener
and more efficient synthetic routes,4 and recent researches
25 have revealed the feasibility to replace transition metal
catalysts with greener and cheaper iodine or iodide reagents.5
For example, Yotphan and coꢀworkers recently reported
iodineꢀcatalyzed oxidative amination of sodium sulfonates.5h
Vinyl sulfones, as key functional units, exhibit a broad
30 range of biological and parmaceutical activities in biological
and medicinal chemistry,6 and show great synthetic value as
building blocks in organic transformations.7 To date various
synthetic methods have been developed,8 mainly including (1)
direct coupling reaction of alkenes or alkynes with sulfone
35 resources (sulfinic acid,9 sodium sulfinate,10 sulfonyl
hydrazide,11 thiols12 and dimethyl sulfoxide5b,13), and (2)
decarboxylative coupling reaction of cinnamic acids with
sodium sulfinate (Scheme 1).14 In Scheme 1, there have been
some new and efficient Pdꢀ or Cuꢀcatalyzed decarbocylative
40 coupling reactions for the synthesis vinyl sulfones from
cinnamic acid and sodium sulfinate. However, all of them
need toxic metals, ligands, oxidants and high temperature
(Scheme 1a–c).
Scheme 1 Methods for synthesis of vinyl sulfones.
It is noteworthy that Jiang’s group has reported a simple and
55 efficient route for the synthesis of vinyl sulfones without any
catalysts (Scheme 1d), and very recently Kuhakarn’s group has
reported a highly efficient method by PhI(OAc)2 mediated
decarboxylative sulfonylation in a very short time (Scheme
1e). However, both of them still suffer from toxic organic
60 solvents and high temperature. It is well known that water as
green reaction medium has practical advantages over organic
solvents and attracted increasing attention in organic
synthesis.15 Herein, we reported a green and efficient method
for the synthesis of vinyl sulfones via I2ꢀmediated
65 decarboxyative crossꢀcoupling reaction of sodium sulfinates
with cinnamic acids, using water as a solvent at lower
temperature.
Firstly, we chose transꢀcinnamic acid (1a) and sodium 4ꢀ
methyl benzenesulfinate (2a) as model substrates to examine
70 various reaction conditions, and the results were shown in
Table 1. We did not get the desired product when the reaction
of 1a with 2a was performed with 1 equiv. of I2 in the absence
of a base at room temperature for 5 h (entry 1). In the
presence of base K2CO3 (1.0 equiv.), (E)ꢀ1ꢀmethylꢀ4ꢀ
75 (styrylsulfonyl)benzene (3a) could be obtained with 10%
yield (entry 2). We attempted to prolong reaction time to 10 h,
but the yield of 3a was not obviously improved (only 23%,
entry 3). Luckily, when the reaction temperature was raised to
40 ºC, the yield of 3a was drastically increased to 72% (entry
80 4). Higher temperatures (50 ºC, 60 ºC and 70 ºC, entries 5–7)
45 School of Chemistry and Chemical Engineering, South China University
of Technology, Guangzhou, 510640, P. R. China
E-mail: gqyuan@scut.edu.cn
This journal is © The Royal Society of Chemistry [year]
[journal], [year], [vol], 00–00 | 1

RSC Advances
Page 2 of 5
View Article Online
DOI: 10.1039/C5RA10896A
were further tested, and a best yield was obtained (91%, entry
30 the other hand, the reactions of transꢀcinnamic acid (1a) with
various sodium sulfinates were tested. Various sodium
sulfinates with 4ꢀH, 4ꢀF, 4ꢀCl and 4ꢀBr groups substituted on
phenyl rings all proceeded smoothly to give good yields
Table 1 Optimization of reaction conditions. a
(78%–83%)
(3p–s).
Moreover,
(E)ꢀ(2ꢀ(methyl
35 sulfonyl)vinyl)benzene (3t) was obtained with 45% yield.
Table 2 Synthesis of (E)ꢀvinyl sulfones. a,b
Entry I2
Base
Solvent Time
(h)
Temp.
(ºC)
Yieldb
(%)
(equiv.) (equiv.)
1
2
3
4
5
6
7
8
1.0
1.0
1.0
1.0
1.0
1.0
1.0
0.5
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
1.0
no
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
5
5
r t
r t
r t
trace
10
23
72
80
91
84
40
41
80
90
14
30
35
22
7
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (0.5)
K2CO3 (2.0)
Cs2CO3(1.0)
NaOAc (1.0)
KOH (1.0)
10
10
10
10
10
10
10
10
10
10
10
10
10
40
50
60
70
60
60
60
60
60
60
60
60
60
60
60
60
60
60
O
S
O
O
S
S
O
O
O
OMe
R
9
3j, 77%
3k, 78%
10
11
12
13
14
15
16
17
18
19
20
21 c
R = H, 3a, 81%
R = Me, 3b, 79%
R = OMe,
R = CN, 3d, 63%
R = F, 3e, 84%
R = Cl, 3f, 84%
R = Br, 3g, 81%
R = CF3, 3h, 80%
R = t-Bu, 3i, 69%
Cl
O
S
O
S
3c, 80%
O
O
CH3ONa(1.0) H2O
Et3N (1.0)
Cl
H2O
CH3CN 10
DMF
EtOAc
CH3OH 10
DMSO
H2O
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
K2CO3 (1.0)
3m, 81%
3l, 77%
10
10
5
3
52
5
87
O
O
R'
S
S
S
O
O
10
10
O
S
N
O
a Reaction conditions: 1a (0.5 mmol), 2a (0.6 mmol), base (1.0 equiv.), I2
(1.0 equiv.), H2O (2 mL) at 60 ºC for 10 h. b Determined by GCꢀMS using
dodecane as the internal standard. c Under N2 atmosphere.
3o, 57%
3n, 55%
O
S
O
R' = H, 3p, 78%
R' = F, 3q, 79%
R' = Cl, 3r, 83%
R' = Br, 3s, 81%
3t, 45%
a
Reaction conditions: 1 (0.5 mmol), 2 (0.6 mmol), I2 (1.0 equiv.),
6). When 0.5 equiv. of I2 or 0.5 equiv. of K2CO3 was added to
the reaction system, the yield of 3a declined to approximately
half of the best yield (entries 8 and 9). Besides, the reaction
efficiency was not improved when excess K2CO3 (2.0 equiv.)
was used (entry 10). At last, various bases (Cs2CO3, NaOAc,
KOH, CH3ONa and Et3N) and solvents (CH3CN, DMF,
EtOAc, CH3OH and DMSO) were screened, respectively.
10 These results showed that K2CO3 was an optimal base and
water was the most suitable solvent in this process (entries
11–20).
With the optimal reaction conditions in hand, the scope of
substrates was investigated and the results are summarized in
15 Table 2. On one hand, we examined the reaction of sodium 4ꢀ
methyl benzenesulfinate (2a) with cinnamic acid derivatives
in the standard reaction conditions. Some cinnamic acids
which have electronꢀwithdrawing substituents on the phenyl
ring (4ꢀCN, 4ꢀF, 4ꢀCl, 4ꢀBr, 4ꢀCF3 and 2,6ꢀ2Cl) could proceed
20 smoothly to afford the corresponding products in available
yields (63%–84%) (3d–h, 3m). Also, cinnamic acids with
electronꢀdonating substituents on the phenyl ring (4ꢀMe, 4ꢀ
MeO, 4ꢀt-Bu, 2ꢀMe, 2ꢀMeO and 3ꢀMe) were examined, and
the yields of the corresponding products ranged from 69% to
25 81% (3b–c, 3i–l). These results did not obviously change in
comparison with those of substrates having electronꢀ
K2CO3 (1.0 equiv.), H2O (2 mL) at 60 ºC for 10 h. b Isolated yields.
5
It is worth noting that the reaction was performed on a
1.0 g scale to afford 3a with 81% yield, indicating that the
reaction is scalable and practical (Scheme 2).
To understand the reaction mechanism better, some
control experiments have been explored. The desired
product 3a was obtained with a good yield under nitrogen
atmosphere, which eliminated the influence of oxygen on
this reaction very well (Table 1, entry 21). The reaction of
40
45 1a with 2a was proceeded under the standard conditions in
the presence of 2,2,6,6ꢀtetramethylꢀ1ꢀpiperidinyloxy
(TEMPO), and no 3a was detected by GC, which implied a
radical pathway should be involved (Scheme 3a). When
using 4ꢀmethylbenzeneꢀ1ꢀsulfonyl iodide as the substrate
50 instead of 2a and iodine, the yield of 3a was almost
unchanged (Scheme 3b). The result suggested that 4ꢀ
methylbenzeneꢀ1ꢀsulfonyl iodide should be an intermediate
in this transformation. The synthetic procedure of 4ꢀ
methylbenzeneꢀ1ꢀsulfonyl iodide was given in the
55 Supporting Information. In addition, it should be pointed out
that I2 is almost converted to iodine anions after the reaction
in two steps (i.e., the reaction of ArSO2Na with I2, and the
reaction of ArSO2I with cinnamic acid) in the present
standard conditions, which is confirmed by iodometric
withdrawing
substituents.
In
addition,
(E)ꢀ2ꢀ(2ꢀ
tosylvinyl)pyridine (3n) and (E)ꢀ2ꢀ(2ꢀtosylvinyl)thiophene (3o)
could be obtained with 55% and 57% yields, respectively. On
2
| Journal Name, [year], [vol], 00–00
This journal is © The Royal Society of Chemistry [year]

Page 3 of 5
RSC Advances
View Article Online
DOI: 10.1039/C5RA10896A
titration.
Based on the results of control experiments, a possible
30 We are grateful to the National Natural Science Foundation of
China (21172079) and the Science and Technology Planning
Project of Guangdong Province (2011B090400031) for
financial support.
reaction mechanism was proposed in Scheme 4. It is easy to
generate intermediate A from sodium sulfinate and iodine,
and the intermediate A undergoes homolysis to give a
sulfonyl radical (B) and an iodine radical.16 Subsequently,
the radical B is added to the double bond of cinnamic acid to
afford intermediate C,14bꢀe,17 which is combined with iodine
or iodine radical to generate intermediate D.10b,d Finally, the
5
Notes and references
35
40
45
50
55
60
65
70
75
80
85
1
For reviews on transitionꢀmetalꢀcatalyzed coupling reactions, please
see: (a) C. C. C. J. Seechurn, M. O. Kiching, T. J. Colacot and V.
Snieckus, Angew. Chem., Int. Ed., 2012, 51, 5062; (b) X. F. Wu, H.
Neumann and M. Beller, Chem. Soc. Rev., 2011, 40, 4986; (c) F. S.
Han, Chem. Soc. Rev., 2013, 42, 5270; (d) R. Jana, T. P. Pathak and
M. S. Sigman, Chem. Rev., 2011, 111, 1417; (e) K. C. Nicolaou, P.
G. Bulger and D. Sarlah, Angew. Chem., Int. Ed., 2005, 44, 4442; (f)
I. Bauer and H. J. Knölker, Chem. Rev., 2015, 115, 3170.
10 intermediate D undergoes the elimination of carbon dioxide
and hydrogen iodide to provide the desired vinyl sulfones
with the help of a base.14c,17
2
For reviews on transitionꢀmetalꢀcatalyzed coupling reactions of CꢀC
bond or Cꢀheteroatom formation, please see: (a) W. Shi, C. Liu and
A. W. lei, Chem. Soc. Rev., 2011, 40, 2761; (b) B. J. Li and Z. J. Shi,
Chem. Soc. Rev., 2012, 41, 5588; (c) R. Kumar and E. V. V. Eycken,
Chem. Soc. Rev., 2013, 42, 1121; (d) S. G. Modha, V. P. Mehta and
E. V. V. Eycken, Chem. Soc. Rev., 2013, 42, 5042; (e) C. Shen, P. F.
Zhang, Q. Sun, S. Q. Bai, T. S. Andy Hor and X. G. Liu, Chem. Soc.
Rev., 2015, 44, 291; (f) G. Cahiez and A. Moyeux, Chem. Rev., 2010,
110, 1435.
15 Scheme 2 Reaction on a 1.0 gram scale.
3
(a) H. Li, L. Wang, Y. Zhang and J. B. Wang, Angew. Chem., Int. Ed.,
2012, 51, 2943; (b) H. Zhang, R. Y. Shi, A. X. Ding, L. J. Lu, B. R.
Chen and A. W. Lei, Angew. Chem., Int. Ed., 2012, 51, 12542; (c) V.
P. Mehta and B. Punji, RSC Advances, 2013, 3, 11957; (d) C. L. Sun
and Z. J. Shi, Chem. Rev., 2014, 114, 9219; (e) S. Roscales and A. G.
Csákÿ, Chem. Soc. Rev., 2014, 43, 8215.
Scheme 3 Control experiments.
4
5
(a) B. A. F. Uribe, R. D. Little, J. G. Ibanez, A. Palma and R. V.
Medrano, Green Chem., 2010, 12, 2099; (b) Y. L. Gu and F. Jérôme,
Chem. Soc. Rev., 2013, 42, 9550; (c) G. L. Sorella, G. Strukul and A.
Scarso, Green Chem., 2015, 17, 644; (d) B. H. Lipshutz and S.
Ghorai, Green Chem., 2014, 16, 3660.
(a) X. J. Pan, J. Gao, J. Liu, J. Y. Lai, H. F. Jiang and G. Q. Yuan,
Green Chem., 2015, 17, 1400; (b) J. Gao, X. J. Pan, J. Liu, J. Y. Lai,
L. M. Chang and G. Q. Yuan, RSC Advances, 2015, 5, 27439; (c) A.
K. Banerjee, W. Vera, H. Mora, M. S. Laya, L. Bedoya and E. V.
Cabrera, J. Sci. Ind. Res., 2006, 65, 299; (d) T. Nobuta, N. Tada, A.
Fujiya, A. Kariya, T. Miura and A. Itoh, Org. Lett., 2013, 15, 574; (e)
M. A. Kumar, P. Swamy, M. Naresh, M. M. Reddy, C. N. Rohitha, S.
Prabhakar, A. V. S. Sarma, J. R. P. Kumar and N. Narender, Chem.
Commun., 2013, 49, 1711; (f) W. Xu, U. Kloeckner and B. J.
Nachtsheim, J. Org. Chem., 2013, 78, 6065; (g) P. R. Adiyala, D.
Chandrasekhar, J. S. Kapure, C. N. Reddy and R. A. Maurya,
Beilstein J. Org. Chem., 2014, 10, 2065; (h) C. Buathongjan, D.
Beukeaw and S. Yotphan, Eur. J. Org. Chem., 2015, 1575.
20
Scheme 4 Possible reaction mechanism.
6
(a) S. Y. Woo, J. H. Kim, M. K. Moon, S. H. Han, S. K. Yeon, J. W.
Choi, B. K. Jang, H. J. Song, Y. G. Kang, J. W. Kim, J. Lee, D. J.
Kim, O. Hwang and K. D. Park, J. Med. Chem., 2014, 57, 1473; (b)
E. Dunny, W. Doherty, P. Evans, J. P. G. Malthouse, D. Nolan and
A. J. S. Knox, J. Med. Chem., 2013, 56, 6638; (c) W. Doherty, J.
James, P. Evans, L. Martin, N. Adler, D. Nolan and A. Knox, Org.
Biomol. Chem., 2014, 12, 7561; (d) B. A. Frankel, M. Bentley, R. G.
Kruger and D. G. McCafferty, J. Am. Chem. Soc., 2004, 126, 3404.
(a) J. Aziz, S. Messaoudi, M. Alami and A. Hamze, Org. Biomol.
Chem., 2014, 12, 9743; (b) M. N. Noshi, A. Elꢀawa, E. Torres and P.
In conclusion, we have developed a green and efficient
method for the synthesis of vinyl sulfones via I2ꢀmediated
decarboxylative coupling reaction using environmentally
25 friendly water as the reaction medium. This reaction shows its
fascinating application prospect in organic synthesis.
Compared with the reported methods, this route seems to be
greener and more efficient.
7
Acknowledgements
This journal is © The Royal Society of Chemistry [year]
Journal Name, [year], [vol], 00–00 | 3

RSC Advances
Page 4 of 5
View Article Online
DOI: 10.1039/C5RA10896A
L. Fuchs, J. Am. Chem. Soc., 2007, 129, 11242; (c) H. M. Li, J. Song,
X. F. Liu and L. Deng, J. Am. Chem. Soc., 2005, 127, 8948.
For reviews on other routes of synthesis of vinyl sulfones, please see:
(a) D. C. Reeves, S. Rodriguez, H. Lee, N. Haddad, D.
Krishnamurthy and C. H. Senanayake, Tetrahedron Lett., 2009, 50,
2870; (b) R. Chawla, R. Kapoor, A. K. Singh and D. S. Yadav,
Green Chem., 2012, 14, 1308; (c) J. L. G. Ruano, J. Alemán and C.
G. Paredes, Org. Lett., 2006, 8, 2683; (d) N. Kamigata, H. Sawada
and M. Kobayashi, J. Org. Chem., 1983, 48, 3793.
8
5
10
15
20
25
30
35
40
9
W. Wei, J. L. Li, D. S. Yang, J. W. Wen, Y. T. Jiao, J. M. You and H.
Wang, Org. Biomol. Chem., 2014, 12, 1861.
10 (a) Y. L. Xu, J. W. Zhao, X. D. Tang, W. Q. Wu and H. F. Jiang, Adv.
Synth. Catal., 2014, 356, 2029; (b) V. Nair, A. Augustine, T. G.
George and L. G. Nair, Tetrahedron Lett., 2001, 42, 6763; (c) Y. C.
Luo, X. J. Pan and G. Q. Yuan, Tetrahedron, 2015, 73, 2119; (d) N.
Zhang, D. S. Yang, W. Wei, L. Yuan, Y. J. Cao and H. Wang, RSC
Advances, 2015, 5, 37013; (e) N. Taniguchi, Tetrahedron, 2014, 70,
1984; (f) N. Taniguchi, Synlett, 2012, 23, 1245; (g) P. Katurn, S.
Chiampanichayakul, K. Korworapan, M. Pohmakotr, V. Reutrakul,
T. Jaipetch and C. Kuhakarn, Eur. J. Org. Chem., 2010, 5633.
11 (a) G. W. Rong, J. C. Mao, H. Yan, Y. Zheng and G. Q. Zhang, J.
Org. Chem., 2015, 80, 4697; (b) X. W. Li, Y. L. Xu, C. Jiang, C. R.
Qi and H. F. Jiang, Chem. Eur. J., 2014, 20, 7911; (c) S. Tang, Y.
Wu, W. Q. Liao, R. P. Bai, C. Liu and A. W. Lei, Chem. Commun.,
2014, 50, 4496.
12 Q. C. Xue, Z. J. Mao, Y. Shi, H. B. Mao, Y. X. Cheng and C. J. Zhu,
Tetrahedron Lett., 2012, 53, 1851.
13 Y. J. Jiang and T. P. Loh, Chem. Sci., 2014, 5, 4939.
14 (a) R. Q. Guo, Q. W. Gui and D. D. Wang, Catal. Lett., 2014, 144,
1377; (b) B. V. Rokade and K. R. Prabhu, J. Org. Chem., 2014, 79,
8110; (c) Q. Jiang, B. Xu, A. Zhao, Y. R. Zhao, Y. Y. Li, N. N. He
and C. C. Guo, J. Org. Chem., 2014, 79, 7372; (d) Y. L. Xu, X. T.
Tang, W. G. Hu, W. Q. Wu and H. F. Jiang, Green Chem., 2014, 16,
3720; (e) P. Katrun, S. Hlekhlai, J. Meesin, M. Pohmakotr, V.
Reutrakul, T. Jaipetch, D. Soorukram and C. Kuhakarn, Org.
Biomol. Chem., 2015, 13, 4785; (f) H. S. Li and G. Liu, J. Org.
Chem., 2014, 79, 509.
15 (a) L. Shi, Y. Y. Liu, Q. F. Liu, B. Wei and G. S. Zhang, Green
Chem., 2012, 14, 1372; (b) M B. Gawande, A. D. B. Bonifácio, P.
S. Branco and R. S. Varma, Chem. Soc. Rev., 2013, 42, 5522; (c) N.
E. Leadbeater, Chem. Commun., 2005, 2881; (d) H. D. Velazquez
and F. Verpoort, Chem. Soc. Rev., 2012, 41, 7032; (e) Y. L. Gu,
Green Chem., 2012, 14, 2091; (f) B. Li and P. H. Dixneuf, Chem.
Soc. Chem., 2013, 42, 5744.
45 16 (a) W. E. Truce and G. C. Wolf, J. Org. Chem., 1971, 36, 1727; (b)
P. Katrun, C. Mueangkaew, M. Pohmakotr, V. Reutrakul, T.
Jaipetch, D. Soorukram and C. Kuhakarn, J. Org. Chem., 2014, 79,
1778; (c) E. Truce, D. L. Heuring and G. C. Wolf, J. Org. Chem.,
1980, 45, 406; (d) L. M. Harwood, M. Julia and G. L. Thuiller,
50
Tetrahedron, 1980, 36, 2483; (e) D. C. Craig, G. L. Edwards and C.
A. Muldoon, Synlett, 1977, 1441.
17 Q. Jiang, J. Jia, A. Zhao and C. C. Guo, J. Org. Chem., 2015, 80,
3586.
4
| Journal Name, [year], [vol], 00–00
This journal is © The Royal Society of Chemistry [year]

Page 5 of 5
RSC Advances
View Article Online
DOI: 10.1039/C5RA10896A
Iodine-mediated synthesis of (E)-vinyl sulfones from sodium
sulfinates and cinnamic acids in aqueous medium
Jian Gao, Junyi Lai and Gaoqing Yuan*
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China
A green and highly efficient method for the synthesis of (E)-vinyl sulfones promoted by iodine in water medium
has been developed, without transition metal catalysts and ligands.