Electrosynthesis of (E)-Vinyl Sulfones Directly from Cinnamic Acids and Sodium Sulfinates via Decarboxylative Sulfono Functionalization

Article abstract of DOI:10.1021/acs.joc.6b00661

A variety of (E)-vinyl sulfones were constructed directly from cinnamic acids and sodium sulfinates with high regioselectivity at room temperature by virtue of an electrocatalytic oxidation. A radical intermediate was detected, and the corresponding mecha

Full text of DOI:10.1021/acs.joc.6b00661

Note
pubs.acs.org/joc
Electrosynthesis of (E)‑Vinyl Sulfones Directly from Cinnamic Acids
and Sodium Sulfinates via Decarboxylative Sulfono Functionalization
Peng Qian, Meixiang Bi, Jihu Su, Zhenggen Zha,* and Zhiyong Wang*
Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of
Chemistry & Collaborative Innovation Center of Suzhou Nano Science and Technology, University of Science and Technology of
China, Hefei, Anhui 230026, P. R. China
S
* Supporting Information
ABSTRACT: A variety of (E)-vinyl sulfones were constructed
directly from cinnamic acids and sodium sulfinates with high
regioselectivity at room temperature by virtue of an electrocatalytic
oxidation. A radical intermediate was detected, and the correspond-
ing mechanism was investigated.
inyl sulfones widely exist in pharmaceutically active
the high yield can be obtained when the 20 mA current was
used (entries 2−4). Subsequently, it was found that the best
anode was the carbon rod, while the best cathode was a
platinum plate (entries 5−10). An investigation of electrolytes
showed that electrolytes had a slight influence on yield (entries
11 and 12). Nevertheless, the solvent had an important
influence on the reaction. For instance, the combination of
CH3CN and H2O (7:1) favored the reaction, while other
solvents disfavored the reaction (entries 13−15). In order to
promote the reaction further, some additives were tested
(entries 16−21). It was found that the appropriate AcOH was
beneficial to this transformation (entries 20−23). A higher
concentration of 2a increased the yield from 75% to 77%
(entries 24 and 25). On the other hand, only a trace amount of
product was detected when the reaction was carried out in an
oxygen atmosphere, while a nitrogen atmosphere led to a
slightly lower yield. Taken together, the optimal conditions
were obtained as below: cinnamic acids (0.5 mmol), sodium
sulfinates (1.2 mmol), n-Bu4NClO4 (1 mmol), AcOH (0.25
mmol), CH3CN/H2O (7/1 mL), carbon rod as the anode,
platinum plate as the cathode. All of the reactions were
electrolyzed at a constant current of 20 mA for 2 h in an
undivided cell at room temperature.
1
Vagents
and naturally active molecules and are the
prevalent molecular skeleton for various organic transforma-
tions.2 The invention of methodologies toward this building
block is a long-standing goal in organic synthesis, and
considerable progress has been made in this area. In terms of
these synthetic methodologies,3 the overwhelming majority
were still not green enough, often involving a high-temperature,
transition-metal catalysis and limited availability of raw
materials. Therefore, a more modern and green strategy for
the broadly rapid electrosynthesize (E)-vinyl sulfones directly
from readily accessible starting materials at room temperature is
still desired. Electrochemical synthesis has been extensively
employed in a variety of chemical transformations and has
become an interesting and attractive avenue for their benign
properties, selectivity, and sustainability.4,5 Our group has
developed a series of electrochemical routes toward various
organic transformations,6 motivating us to accomplish a sulfo
functionalization via an electrochemical decarboxylation
oxidation. The reaction can be carried out directly from facile
cinnamic acids and sodium sulfinates at room temperature
under an elegant constant current with good selectivity and
yield. As far as we know, this electrocatalytic decarboxylation
coupling should be one of the best efficient methods to
construct the (E)-vinyl sulfones under the mild conditions.
We commenced our studies by attempting the proposed
decarboxylative coupling of cinnamic acid 1a with sodium
sulfinates 2a in an undivided cell at room temperature. As
shown in Table 1 (entry 1), the proposed decarboxylation sulfo
functionalization was conducted smoothly via an electro-
catalytic oxidation. The current optimization indicated that
Having identified the optimized conditions for this electro-
catalytic decarboxylative coupling, we then examined the
compatibility of this reaction with respect to cinnamic acids
and sodium sulfinates (Table 2). As shown in Table 2, a broad
scope of cinnamic acids was found, and the cinnamic acids with
Received: March 31, 2016
Published: May 13, 2016
© 2016 American Chemical Society
4876
DOI: 10.1021/acs.joc.6b00661
J. Org. Chem. 2016, 81, 4876−4882

The Journal of Organic Chemistry
Note
a
Table 1. Optimization of the Reaction Conditions
b
entry
electrode (anode/cathode)
electrolyte
additive (equiv)
current (mA)
solvent (mL)
yield (%)
1
Pt/Pt
Pt/Pt
Pt/Pt
Pt/Pt
C/Pt
C/C
LiClO4
LiClO4
LiClO4
LiClO4
LiClO4
LiClO4
LiClO4
LiClO4
LiClO4
LiClO4
none
40
30
20
10
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
MeOH/H2O
EtOH/H2O
26
35
2
none
3
none
43
4
none
41
5
none
66
6
none
25
7
C/Ag
C/Au
C/Ti
C/Zn
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
C/Pt
none
52
8
none
55
9
none
50
10
11
12
13
14
15
16
17
18
19
20
21
22
23
none
40
n-Bu4NClO4
n-Bu4NPF6
none
67
none
66
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
n-Bu4NClO4
none
trace
trace
trace
61
none
none
THF/H2O
Et3N (0.5)
DBU (0.5)
HFIP (0.5)
CF3CH2OH (0.5)
AcOH (0.5)
H3PO4 (0.5)
AcOH (0.25)
AcOH (1)
AcOH (0.5)
AcOH (0.5)
AcOH (0.5)
AcOH (0.5)
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
CH3CN/H2O
60
73
34
75
trace
68
65
c
24
77
d
25
70
e
26
trace
73
f
27
a
Reaction conditions: 1a (0.5 mmol), 2a (1.0 mmol), electrolyte (1 mmol), solvent/H2O = 7:1 (8 mL); the electrolysis was conducted at a constant
b
c
d
e
current for 2 h in an undivided cell. Yields of the isolated products. 1.2 mmol of 2a was used. 1.5 mmol of 2a was used. O2 was used instead of
air. N2 was used instead of air. HFIP: 1,1,1,3,3,3-hexafluoro-2-propanol.
f
different substituents were readily converted to the correspond-
ing (E)-vinyl sulfones with moderate to good yields. Never-
theless, both the steric effect and the electronic effect of the
substituents were observed in the reaction. Generally, the ortho
substitution on the phenyl ring of the cinnamic acids disfavored
this reaction in comparison with the meta and para
substitutions (3n vs 3j and 3b; 3o vs 3k and 3c; 3p vs 3m
and 3e 3q vs 3f). This implied that the hindrance had a
negative influence on this reaction. On the other hand, the
electron-rich cinnamic acids were more reactive than electron-
deficient ones (3b,c vs 3g−i), while weak electron-withdrawing
(F, Cl, Br, 3d−f) groups had little influence on the reaction
yield. To our delight, the sterically congested substrate 1-
naphthalene and multisubstituted cinnamic acid could proceed
smoothly in this transformation, albeit with a slightly lower
yield (3r and 3s). However, ferulic acid gave a trace amount of
product due to the effect of hydroxyl group. Further, pyridines,
furans, and thiophenes were also good substrates in the
reaction, affording the corresponding desired product in 45−
67% yield (3u−w). Besides, when β-methyl- and phenyl-
substituted cinnamic acid derivatives were used as the starting
materials, the corresponding yields of the product were 62%
and 50% (3x and 3y), respectively. Nevertheless, α-methyl-
substituted cinnamic acid gave a trace amount of the desired
product, perhaps due to the steric hindrance. 2-Cyclo-
hexylideneacetic acid was also examined in this reaction, no
desired product was detected. In order to extend the scope of
unsaturated acid substrate, phenylpropiolic acid was employed
as the reaction substrate to give (phenylethynylsulfonyl)-
benzene 3ab smoothly, although the reaction afforded the
product with a low yield of 29%. Finally, the scope of sodium
sulfinates was also investigated. The electronic effect and steric
hindrance of sodium phenylsulfinates had a great influence on
the reaction, although the weak electron-donating sodium 4-
toluenesulfinate and electron-withdrawing sodium 4-chloro-
benzenesulfinate could provide the vinyl sulfones in 81% and
40% yield (3ac and 3ad), respectively. When the more
electron-rich (4-MeO) and electron-deficient (4-NO2) sodium
phenylsulfinates were used as substrates, the reactions hardly
proceeded and gave a trace amount of the desired product (see
details in the Supporting Information). The sodium mesityle-
nesulfinate could not give the desired product either, perhaps
due to the steric hindrance. On the other hand, aliphatic
sodium sulfinates (e.g., sodium methanesulfinate and sodium
trifluoromethanesulfinate) were not compatible under the
reaction conditions and no desired products were detected,
perhaps due to the instability of the intermediate A.
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DOI: 10.1021/acs.joc.6b00661
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The Journal of Organic Chemistry
Note
1a), suggesting the reaction presumably involved a radical
pathway. When styrene was employed as the coupling partner
under the standard conditions, only a trace amount of vinyl
sulfone was obtained, which implied styrene was not the mainly
active intermediate of this reaction (Scheme 1b). Moreover,
when methyl cinnamate and 2a was carried out under the
standard reaction conditions, the expected product was not
detected, and almost all of the methyl cinnamate was recovered
(Scheme 1c), which indicated that the carboxyl group was
necessary for the reaction.
Table 2. Substrate Scope for the Decarboxylative Sulfono
Functionalization
a
In an attempt to better understand this reaction, the EPR
spin trapping and cyclic voltammetry (CV) were undertaken to
monitor this progress. In the EPR experiments (Figure 1), 5,5-
dimethyl-1-proline N-oxide (DMPO) was used to trap the
potentially involved free radicals. As expected, the experimental
EPR spectra (a) and the corresponding simulations (b−d) were
achieved. The spectrum b was identified according to the
hyperfine coupling constants for the nitrogen (A14N = 16.2 G)
and the β-proton (A1H = 25.2 G), indicating the radical was
centered at a carbon group between single and double bonds.7
Another signal (c) was found to be the radical •OH,
characterized by the hyperfine coupling constants for the
nitrogen (A14N = 14.7 G) and the β-proton (A1H = 14.7 G).7
When we overlapped the spectra b and c, the complicated
spectrum d was formed, matching the experimental result (a).
From the cyclic voltammogram (Figure 2), three oxidation
waves were easily observed. One at 1.03 V was assigned to the
oxidation of sodium sulfinates to sulfonyl radical, and the other,
1.73 V, was attributed to the oxidation of sulfonyl radical.
Another, 2.20 V was also obtained, corresponding to the
oxidation of cinnamic acid and water.8
In light of the mentioned experiments and preceding
literature,3f,9 a possible radical-based pathway is presented as
shown in Scheme 2. A sulfonyl radical intermediate A is
generated by the oxidation of sodium sulfinates in the anodic
electrode and then is attacked by anion B to give rise to anion
radical C, which is easy to be decarboxylated to afford the vinyl
sulfone 3a under the reaction conditions.
In conclusion, we developed an electrochemical decarbox-
ylative sulfono functionalization protocol and demonstrated its
utility directly from readily available starting materials at room
temperature with high regioselectivity and good functional
group tolerance, utilizing electrons as oxidant. Based on the
EPR and CV experiments, a radical-based pathway was
proposed.
EXPERIMENTAL SECTION
■
General Information. All products were characterized by 1H
NMR and 13C NMR, using TMS as an internal reference (1H NMR:
400 MHz, 13C NMR: 100 MHz). HRMS (ESI) data were recorded on
a Q-TOF Premier. Commercial reagent and compound were used
without purification unless otherwise indicated. Various sodium
sulfinates (sodium 4-methoxybenzenesulfinate, sodium 4-nitrobenze-
nesulfinate, and sodium mesitylenesulfinate),3f β-methyl-,10,11 β-
phenyl-,10,11 and α-methyl-substituted11,12 cinnamic acid derivatives
as well as 2-cyclohexylideneacetic acid10,11 were prepared according to
literature procedures.
a
Reaction conditions: 1 (0.5 mmol), 2 (1.2 mmol), n-Bu4NClO4 (1.0
mmol), AcOH (0.25 mmol), CH3CN/H2O = 7:1 (8 mL). The
electrolysis was conducted at a constant current of 20 mA about 2 h in
an undivided cell at room temperature. nd: not detected.
Representative Procedures for the Synthesis of (E)-Vinyl
Sulfones. A mixture of cinnamic acid derivatives (0.5 mmol), sodium
sulfinates (1.2 mmol), n-Bu4NClO4 (1 mmol), AcOH (0.25 mmol),
and CH3CN/H2O (7/1 mL) was added to an undivided cell. The cell
was equipped with carbon rod (d = 6 mm) as the anode with a
platinum plate (1.5 × 1.5 cm2) as the cathode. The reaction mixture
was stirred and electrolyzed at a constant current of 20 mA under
room temperature for 2 h. When the reaction was finished, the solvent
To gain insight into the reaction mechanism, some control
experiments were conducted (Scheme 1). First, the reaction
was completely inhibited with the addition of 2,2,6,6-
tetramethyl-1-piperidinyloxy (TEMPO, 2.4 equiv) (Scheme
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DOI: 10.1021/acs.joc.6b00661
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The Journal of Organic Chemistry
Note
Scheme 1. Control Experiments for the Reaction
Figure 2. Cyclic voltammogram curves of 1a, 2a and AcOH in the
solution of 0.125 M n-Bu4NClO4/CH3CN/H2O = 7:1 (8 mL), using
GC disk as working electrode, Pt wire, and Ag/AgCl as counter and
reference electrode at 50 mV/s scan rate: (e) 1a (0.0625 M), 2a (0.15
M) and AcOH (0.03125 M); (f) 1a (0.0625 M) and 2a (0.15 M); (h)
1a (0.0625 M); (i) 2a (0.15 M); (k) 0.125 M n-Bu4NClO4/CH3CN/
H2O.
Figure 1. EPR spectra (X band, 9.7 GHz, room temperature) for
reaction mixtures in the presence of the radical trapper DMPO. The
complicated spectrum (a) is the experimental spectrum, and the others
(b−d) were their simulations. Spectra b and c were assigned to a
carbon group radical between single and double bonds and the radical
•OH, respectively, while the complicated spectrum (d) was the
overlapping of spectra b and c.
Scheme 2. Proposed Reaction Mechanism
was removed with a rotary evaporator. The solution was then added to
9 mL of water and extracted with EtOAc (3 × 10 mL). The combined
organic layer was dried with Na2SO4 and filtered. The solvent was
removed with a rotary evaporator. The residue was purified by column
chromatography on silica, and the product was dried under high
vacuum for at least 0.5 h before it was weighed and characterized by
NMR spectroscopy.
Experimental Details for the Capture of Radical. An undivided
cell was equipped with a magnet stirrer, carbon rod (d = 6 mm) as the
anode, and a platinum plate (1.5 × 1.5 cm2) as the cathode,
respectively. In the electrolytic cell, a solution of cinnamic acid (0.5
mmol), sodium sulfinates (1.2 mmol), n-Bu4NClO4 (1 mmol), AcOH
(0.25 mmol), N2 (balloon), and CH3CN/H2O (7/1 mL) was allowed
to stir and electrolyze at a constant current of 20 mA for 40 min at 0
°C. A 0.05 mL portion of solution was added to a small tube and
mixed well with 0.03 mL of DMPO. The mixture was quick-frozen
with liquid nitrogen and measured at room temperature by EPR.
(E)-[2-(Phenylsulfonyl)vinyl]benzene (3a).3g The title compound
was prepared according to the general working procedure and purified
by column chromatography (petroleum ether/ethyl acetate = 10:1) to
give the product as a colorless solid: 77% yield (94.1 mg); mp = 62−
63 °C; 1H NMR (CDCl3, 400 MHz) δ 7.97−7.94 (m, 2H), 7.69 (d, J
= 15.4 Hz, 1H), 7.64−7.60 (m, 1H), 7.57−7.53 (m, 2H), 7.50−7.48
(m, 2H), 7.42−7.37 (m, 3H), 6.86 (d, J = 15.4 Hz, 1H); 13C NMR
4879
DOI: 10.1021/acs.joc.6b00661
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Note
(CDCl3, 100 MHz) δ 142.5, 140.8, 133.4, 132.4, 131.2, 129.3, 129.1,
128.6, 127.7, 127.3; IR (KBr) 3044, 2918, 1611, 1574, 1446, 1298,
1142, 1084 cm−1; HRMS calcd [C14H12O2S + Na]+ 267.0456, found
267.0458.
(E)-1-(Trifluoromethyl)-4-(2-(phenylsulfonyl)vinyl)benzene (3h).3k
The title compound was prepared according to the general working
procedure and purified by column chromatography (petroleum ether/
ethyl acetate = 10:1) to give the product as a yellow oil: 54% yield
(E)-1-Methyl-4-[2-(phenylsulfonyl)vinyl]benzene (3b).3g The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as colorless solid: 84% yield (108.0
1
(85.0 mg); H NMR (CDCl3, 400 MHz) δ 7.98−7.95 (m, 2H), 7.71
(d, J = 15.4 Hz, 1H), 7.67−7.63 (m, 3H), 7.61−7.56 (m, 4H), 6.96 (d,
J = 15.5 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 140.4, 140.1, 135.7,
133.7, 132.6(d, J = 32.5 Hz), 130.0, 129.5, 128.8, 127.8, 126.1 (q, J =
3.7 Hz), 123.6 (d, J = 270.9 Hz); IR (KBr) 3064, 2925, 1613, 1383,
1325, 1169, 1120, 1067, 845, 750 cm−1; HRMS calcd [C15H11F3O2S +
Na]+ 335.0330, found 335.0325.
1
mg); mp = 118−120 °C; H NMR (CDCl3, 400 MHz) δ 7.96−7.93
(m, 2H), 7.66 (d, J = 15.4 Hz, 1H), 7.61−7.59 (m, 1H), 7.56−7.52
(m, 2H), 7.38 (d, J = 8.08 Hz, 2H), 7.19 (d, J = 8.04 Hz, 2H), 6.81 (d,
J = 15.4 Hz, 1H), 2.37 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 142.6,
141.9, 140.9, 133.3, 129.8, 129.6, 129.3, 128.6, 127.6, 126.0. 21.5; IR
(KBr) 3053, 2918, 1604, 1510, 1446, 1306, 1143, 1082 cm−1; HRMS
calcd [C15H14O2S+ Na]+ 281.0612, found 281.0610.
(E)-1-(Trifluoromethyl)-3-(2-(phenylsulfonyl)vinyl)benzene (3i).3l
The title compound was prepared according to the general working
procedure and purified by column chromatography (petroleum ether/
ethyl acetate = 10:1) to give the product as a colorless solid: 60% yield
(E)-1-Methoxy-4-[2-(phenylsulfonyl)vinyl]benzene (3c).3g The
title compound was prepared according to the general working
procedure and purified by column chromatography (petroleum ether/
ethyl acetate = 10:1) to give the product as a colorless solid: 80% yield
(109.9 mg); mp = 100−101 °C; 1H NMR (CDCl3, 400 MHz) δ 7.96−
7.93 (m, 2H), 7.64 (d, J = 15.4 Hz, 1H), 7.61−7.59 (m, 1H), 7.56−
7.52 (m, 2H), 7.45−7.42 (m, 2H), 6.91−6.89 (m, 2H), 6.72 (d, J =
15.4 Hz, 1H), 3.83 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 162.1,
142.3, 141.1, 133.2, 130.4, 129.3, 127.5, 125.0, 124.4, 114.5, 55.5; IR
(KBr) 3061, 2939, 2846, 1601, 1509, 1444, 1260, 1138, 1081 cm−1;
HRMS calcd [C15H14O3S + Na]+ 297.0561, found 297.0559.
1
(93.0 mg); mp = 83−85 °C; H NMR (CDCl3, 400 MHz) δ 7.98−
7.95 (m, 2H), 7.73 (s, 1H), 7.69−7.63 (m, 4H), 7.59−7.52 (m, 3H),
6.95 (d, J = 15.5 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 140.5,
140.2, 133.7, 133.2, 131.9, 131.7, 131.5, 129.7, 129.5, 127.8, 127.6 (q, J
= 3.7 Hz), 125.0 (q, J = 3.7 Hz), 122.2; IR (KBr) 3071, 2924, 1621,
1446, 1431, 1325, 1301, 1139, 1068 cm−1; HRMS calcd [C15H11F3O2S
+ Na]+ 335.0330, found 335.0331.
(E)-1-Methyl-3-[2-(phenylsulfonyl)vinyl]benzene (3j).3f The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a pale yellow solid: 87% yield
(112.1 mg); mp = 105−106 °C; 1H NMR (CDCl3, 400 MHz) δ 7.96−
7.94 (m, 2H), 7.66(d, J = 15.4 Hz, 1 H), 7.62−7.59 (m, 1H), 7.56−
7.53 (m, 2H), 7.29−7.26(m, 3H), 7.23−7.21 (m, 1H), 6.85(d, J = 15.4
Hz, 1H), 2.35(s, 3H); 13C NMR (CDCl3, 100 MHz) δ 142.7, 140.8,
138.9, 133.3, 132.3, 132.1, 129.3, 129.1, 129.0, 127.6. 127.0, 125.8,
21.3; IR (KBr) 3048, 2923, 1614, 1445, 1384, 1260, 1143, 1084, 747,
621 cm−1; HRMS calcd [C15H14O2S + Na]+ 281.0612, found
281.0613.
(E)-1-Fluoro-4-[2-(phenylsulfonyl)vinyl]benzene (3d).3g The title
compound was prepared according to the general working procedure
and purified by column chromatography to give the product
(petroleum ether/ethyl acetate = 10:1) as a colorless solid: 70%
1
yield (92.2 mg); mp = 92−93 °C; H NMR (CDCl3, 400 MHz) δ
7.97−7.94 (m, 2H), 7.68−7.62 (m, 2H), 7.58−7.54 (m, 2H), 7.51−
7.47 (m, 2H), 7.11−7.06 (m, 2H), 6.80 (d, J = 15.4 Hz, 1H); 13C
NMR (CDCl3, 100 MHz) δ 164.4 (d, J = 251.5 Hz), 141.2, 140.6,
133.5, 130.6 (d, J = 8.7 Hz), 129.4, 128.6 (d, J = 3.4 Hz), 127.6, 127.0
(d, J = 2.2 Hz), 116.4 (d, J = 22.0 Hz); IR (KBr) 3048, 1613, 1599,
1509, 1446, 1302, 1280, 1230, 1141, 1082 cm−1; HRMS calcd
[C14H11FO2S + Na]+ 285.0361, found 285.0361.
(E)-1-Methoxy-3-[2-(phenylsulfonyl)vinyl]benzene (3k).3j The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a colorless solid: 80% yield
(110.0 mg); mp = 101−102 °C; 1H NMR (CDCl3, 400 MHz) δ 7.95
(d, J = 7.2 Hz, 1H), 7.67−7.61 (m, 2H), 7.55 (t, J = 7.9 Hz, 2H), 7.30
(t, J = 7.9 Hz, 2H), 7.08 (d, J = 7.6 Hz, 1H), 6.99−6.95 (m, 2H), 6.85
(d, J = 15.4 Hz, 1H), 3.81 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ
160.0, 142.5, 140.7, 133.7, 133.4, 130.1, 129.4, 127.7, 127.5, 121.2,
117.1, 113.4, 55.4; IR (KBr) 3075, 3046, 3005, 2838, 1598, 1584,
1446, 1300, 1270, 1144, 1083 cm−1; HRMS calcd [C15H14O3S + Na]+
297.0561, found 297.0558.
(E)-1-Chloro-4-[2-(phenylsulfonyl)vinyl]benzene (3e).3g The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a white solid: 76% yield (105.0
1
mg); mp = 128−130 °C; H NMR (CDCl3, 400 MHz) δ 7.96−7.94
(m, 2H), 7.66−7.62 (m, 2H), 7.62−7.60 (m, 1H), 7.58−7.56 (m, 2H),
7.54−7.52 (m, 2H), 6.85 (d, J = 15.4 Hz, 1H); 13C NMR (CDCl3, 100
MHz) δ 141.0, 140.4, 137.2, 133.5, 130.8, 129.7, 129.4, 129.4, 127.9,
127.7; IR (KBr) 3054, 1741, 1614, 1445, 1307, 1146, 1083 cm−1;
HRMS calcd [C14H11ClO2S + Na]+ 301.0066, found 301.0063.
(E)-1-Bromo-4-[2-(phenylsulfonyl)vinyl]benzene (3f).3g The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a colorless solid: 71% yield
(E)-1-Fluoro-3-[2-(phenylsulfonyl)vinyl]benzene (3l). The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a colorless oil: 74% yield (96.9
1
mg); H NMR (CDCl3, 400 MHz) δ 7.97−7.94 (m, 2H), 7.67−7.62
1
(m, 2H), 7.59−7.54 (m, 2 H), 7.40−7.35 (m, 1H), 7.28−7.26 (m,
1H), 7.19−7.16 (m, 1H), 7.14−7.09 (m, 1H), 6.87 (d, J = 15.4 Hz,
1H); 13C NMR (CDCl3, 100 MHz) δ 162.9 (d, J = 246.5 Hz), 141.0
(d, J = 2.5 Hz), 140.3, 134.5 (d, J = 7.7 Hz), 133.6, 130.7 (d, J = 8.3
Hz), 129.4, 128.8, 127.8, 124.6 (d, J = 2.9 Hz), 118.1 (d, J = 21.4 Hz),
114.8 (d, J = 22.0 Hz); IR (KBr) 3061, 1614, 1581, 1555, 1485, 1446,
1304, 1262, 1230, 1145, 1084 cm−1. HRMS calcd [C14H11FO2S +
Na]+ 285.0361, found 285.0359.
(115.0 mg); mp 138−139 °C H NMR (CDCl3, 400 MHz) δ 7.96−
7.94 (m, 2H), 7.66−7.63 (m, 1H), 7.62−7.60 (m, 1H), 7.58−7.56 (m,
2H), 7.54−7.51 (m, 2H), 7.36−7.34 (m, 2H), 6.86 (d, J = 15.4 Hz,
1H); 13C NMR (CDCl3, 100 MHz) δ 141.1, 140.4, 133.6, 132.4,
131.3, 129.9 129.4, 128.0, 127.7, 125.7; IR (KBr) 3054, 1610, 1582,
1481, 1446, 1397, 1305, 1141, 1067 cm−1; HRMS calcd [C14H11BrO2S
+ Na]+ 344.9561, found 344.9562.
(E)-1-Nitro-4-(2-(phenylsulfonyl)vinyl)benzene (3g).3g The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 8:1) to give the product as a yellow solid: 26% yield (37.6
(E)-1-Chloro-3-[2-(phenylsulfonyl)vinyl]benzene (3m). The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a colorless solid: 69% yield (95.8
1
mg); mp = 152−153 °C; H NMR (CDCl3, 400 MHz) δ 8.27−8.24
1
mg); mp = 103−105 °C; H NMR (CDCl3, 400 MHz) δ 7.97−7.94
(m, 2H), 7.98−7.96 (m, 2H), 7.73 (d, J = 15.4 Hz, 1H), 7.69−7.64
(m, 3H), 7.61−7.57 (m, 2H), 7.01 (d, J = 15.5 Hz, 1H); 13C NMR
(CDCl3, 100 MHz) δ 149.0, 139.8, 139.2, 138.4, 133.9, 131.7, 129.6,
129.2, 127.9, 124.3; IR (KBr) 3055, 1592, 1509, 1446, 1337, 1307,
1148, 1085 cm−1; HRMS calcd [C14H11NO4S + Na]+ 312.0306, found
312.0304.
(m, 2H), 7.66−7.54 (m, 4H), 7.47 (d, J = 1.7 Hz, 1H), 7.40−7.31 (m,
3H), 6.88 (d, J = 15.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 140.7,
140.3, 135.1, 134.1, 133.6, 131.1, 130.3, 129.4, 128.9, 128.2, 127.8,
126.8; IR (KBr) 3059, 1617, 1565, 1446, 1322, 1305, 1147, 1086
cm−1; HRMS calcd [C14H11ClO2S + Na]+ 301.0066, found 301.0063.
4880
DOI: 10.1021/acs.joc.6b00661
J. Org. Chem. 2016, 81, 4876−4882

The Journal of Organic Chemistry
Note
(E)-1-Methyl-2-[2-(phenylsulfonyl)vinyl]benzene (3n).3m The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a white solid: 77% yield (100.2
(E)-2-(2-(Phenylsulfonyl)vinyl)pyridine (3u).3g The title compound
was prepared according to the general working procedure and purified
by column chromatography (petroleum ether/ethyl acetate = 10:1) to
give the product as a colorless solid: 45% yield (55.0 mg); mp = 85−
86 °C; 1H NMR (CDCl3, 400 MHz) δ 8.61 (d, J = 4.6 Hz, 1H), 7.98−
7.96 (m, 2H), 7.76−7.72 (m, 1H), 7.68−7.60 (m, 2H), 7.57−7.53 (m,
2H), 7.48−7.41 (m, 2H), 7.31−7.27 (m, 1H), 6.85 (d, J = 15.4 Hz,
1H); 13CNMR (CDCl3, 100 MHz) δ 151.0, 150.3, 140.5, 140.2, 137.1,
133.6, 131.8, 129.4, 127.8, 125.5, 125.0; IR (KBr) 3056, 1579, 1443,
1428, 1309, 1299, 1142, 1082 cm−1; HRMS calcd [C13H11NO2S +
Na]+ 268.0408, found 268.0410.
1
mg); mp = 112−115 °C; H NMR (CDCl3, 400 MHz) δ 7.99−7.94
(m, 3H), 7.65−7.60 (m, 1H), 7.57−7.53 (m, 2H), 7.44 (d, J = 7.8 Hz,
1H), 7.32−7.28 (m, 1H), 7.23−7.17 (m, 2H), 6.79 (d, J = 15.3 Hz,
1H), 2.46(s, 3H); 13C NMR (CDCl3, 100 MHz) δ 140.8, 140.2, 138.2,
133.4, 131.3, 131.1, 130.9, 129.3, 128.2, 127.7. 126.9, 126.5, 19.8; IR
(KBr) 3057, 1612, 1598, 1481, 1446, 1306, 1144, 1085 cm−1; HRMS
calcd [C15H14O2S + Na]+ 281.0612, found 281.0610.
(E)-2-(2-(Phenylsulfonyl)vinyl)furan (3v).3g The title compound
was prepared according to the general working procedure and purified
by column chromatography (petroleum ether/ethyl acetate = 10:1) to
(E)-1-Methoxy-2-[2-(phenylsulfonyl)vinyl]benzene (3o).3f The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a pale yellow solid: 78% yield
1
give the product as a brown viscous oil: 47% yield (55.0 mg); H
1
NMR (CDCl3, 400 MHz) δ 7.95−7.92 (m, 2H), 7.63−7.59 (m, 1H),
7.56−7.52 (m, 2H), 7.48−7.43 (m, 2H), 6.75 (d, J = 15.0 Hz, 1H),
6.71 (d, J = 3.4 Hz, 1H), 6.49−6.48 (m, 1H); 13CNMR (CDCl3, 100
MHz) δ 148.7, 145.7, 140.9, 133.3, 129.3, 128.9, 127.6, 124.7, 117.0,
112.6; IR (KBr) 3058, 1781, 1722, 1621, 1446, 1304, 1138, 1082 cm−1.
HRMS calcd [C12H10O3S + Na]+ 257.0248, found 257.0244.
(107.0 mg); mp = 97−98 °C; H NMR (CDCl3, 400 MHz) δ 7.97−
7.94 (m, 2H), 7.90 (d, J = 15.5 Hz, 1H), 7.62−7.58 (m, 1H), 7.55−
7.51 (m, 2H), 7.43−7.36 (m, 2H), 7.08 (d, J = 15.5 Hz, 1H), 6.98−
6.91 (m, 2H), 3.88 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 158.9,
141.2, 138.6, 133.1, 132.5, 130.8, 129.2, 127.9, 127.6, 121.2, 120.8,
111.3, 55.5; IR (KBr) 3052, 2920, 1648, 1465, 1385, 1277, 1142, 1023,
766, 638 cm−1; HRMS calcd [C15H14O3S + Na]+ 297.0561, found
297.0558.
(E)-2-(2-(Phenylsulfonyl)vinyl)thiophene (3w).3g The title com-
pound was prepared according to the general working procedure and
purified by column chromatography (petroleum ether/ethyl acetate =
10:1) to give the product as a brown solid: 67% yield (83.9 mg); mp =
(E)-1-Chloro-2-[2-(phenylsulfonyl)vinyl]benzene (3p).3f The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a pale yellow solid: 66% yield
(91.9 mg); mp = 75−76 °C; 1H NMR (CDCl3, 400 MHz) δ 8.09 (d, J
= 15.4 Hz, 1H), 7.99−7.96 (m, 2H), 7.66−7.62 (m, 1H), 7.58−7.54
(m, 2H), 7.51 (dd, J1 = 7.8 Hz, J2 = 1.7 Hz, 1H), 7.43 (dd, J1 = 8 Hz, J2
= 1.3 Hz, 1H), 7.36−7.31 (m, 1H), 7.28−7.24 (m, 1H), 6.91 (d, J =
15.5 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 140.3, 138.4, 135.3,
133.6, 131.9, 130.7, 130.4, 130.1, 129.4, 128.3, 127.8, 127.2; IR (KBr)
3054, 2925, 1610, 1449, 1319, 1277, 1146, 1040, 820, 766 cm−1;
1
79−80 °C; H NMR (CDCl3, 400 MHz) δ 7.95−7.93 (m, 2H), 7.80
(d, J = 15.1 Hz, 1H), 7.64−7.60 (m, 1H), 7.57−7.53 (m, 2H), 7.44 (d,
J = 5.0 Hz, 1H), 7.32 (d, J = 3.4 Hz, 1H), 7.08−7.06 (m, 2H);
13CNMR (CDCl3, 100 MHz) δ 140.8, 137.0, 135.2, 133.4, 132.5,
130.1, 129.4, 128.4, 127.6, 125.4; IR (KBr) 3119, 3038, 2919, 1599,
1443, 1418, 1306, 1279, 1141, 1081 cm−1; HRMS calcd [C12H10O2S2
+ Na]+ 273.0020, found 273.0018.
(E)-((2-Phenylprop-1-en-1-yl)sulfonyl)benzene(3x).3i The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 15:1) to give the product as a colorless oil: 60% yield (79.8
mg); 1H NMR (CDCl3, 400 MHz) δ = 8.01−7.98 (m, 2H), 7.66−7.61
(m, 1H), 7.59−7.55 (m, 2H), 7.52−7.35 (m, 5H), 6.62 (d, J = 1.2 Hz,
1H), 2.54 (d, J = 1.2 Hz, 3H); 13C NMR (CDCl3, 100 MHz) δ 152.5,
141.1, 139.1, 132.2, 128.9, 128.2, 127.7, 126.4, 126.2, 125.3, 16.2.
(2-(Phenylsulfonyl)ethene-1,1-diyl)dibenzene (3y).13 The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 15:1) to give the product as a colorless oil: 50% yield (80.0
HRMS calcd [C14H11ClO S + Na]+ 301.0066, found 301.0063.
2
(E)-1-Bromo-2-[2-(phenylsulfonyl)vinyl]benzene (3q). The title
compound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a colorless solid: 67% yield
(108.0 mg); mp = 97−99 °C; 1H NMR (CDCl3, 400 MHz) δ 8.06 (d,
J = 15.4 Hz, 1H), 7.99−7.96 (m, 2H), 7.67−7.61 (m, 2H), 7.59−7.55
(m, 2H), 7.49 (dd, J1 = 7.7 Hz, J2 = 1.8 Hz, 1H), 7.33−7.29 (m, 1H),
7.27−7.23 (m, 1H), 6.85 (d, J = 15.4 Hz, 1H); 13CNMR (CDCl3, 100
MHz) δ 141.0, 140.3, 133.6, 133.6, 132.5, 132.1, 130.2, 129.4, 128.3,
127.9, 125.6; IR (KBr) 3054, 2920, 2850, 1603, 1464, 1305, 1146,
1085 cm−1; HRMS calcd [C14H11BrO2S + Na]+ 344.9561, found
344.9558.
(E)-1-(2-(Phenylsulfonyl)vinyl)naphthalene (3r). The title com-
pound was prepared according to the general working procedure and
purified by column chromatography (petroleum ether/ethyl acetate =
10:1) to give the product as a white solid: 76% yield (112.0 mg); mp =
99−101 °C; 1H NMR (CDCl3, 400 MHz) δ 8.53 (d, J = 15.2 Hz, 1H),
8.16 (d, J = 8.4 Hz, 1 H), 8.03−8.00 (m, 2H), 7.92−7.86 (m, 2H),
7.67−7.53 (m, 6H), 7.45 (t, J = 7.72 Hz, 1H), 6.97 (d, J = 15.2 Hz,
1H); 13C NMR (CDCl3, 100 MHz) δ 140.6, 139.5, 133.7, 133.5,
131.5, 131.3, 129.6, 129.5, 129.4, 128.9, 127.8, 127.4, 126.5, 125.7,
125.3, 123.0; IR (KBr) 3055, 2922, 1604, 1510, 1445, 1304, 1144,
1084 cm−1; HRMS calcd [C18H14O2S + Na]+ 317.0612, found
317.0609.
1
mg); H NMR (CDCl3, 400 MHz) δ 7.52−7.50 (m, 2H), 7.43−7.39
(m, 1H), 7.30−7.25 (m, 5H), 7.21−7.19 (m, 3H), 7.15−7.13 (m, 2H),
7.01−6.99 (m, 2H), 6.95 (s, 1H); 13C NMR (CDCl3, 100 MHz) δ
155.2, 141.5, 139.1, 135.5, 132.8, 130.3, 129.8, 128.9, 128.8, 128.7,
128.6, 128.2, 127.9, 127.6.
(Phenylethynylsulfonyl)benzene (3ab). The title compound was
prepared according to the general working procedure and purified by
column chromatography (petroleum ether/ethyl acetate = 10:1) to
1
give the product as a colorless oil: 29% yield (35.0 mg); H NMR
(CDCl3, 400 MHz) δ 8.10−8.08 (m, 2H), 7.72−7.68 (m, 1H), 7.63−
7.59 (m, 2H), 7.54−7.46 (m, 3H), 7.39−7.36(m, 2H); 13C NMR
(CDCl3, 100 MHz) δ 141.8, 134.2, 132.8, 131.6, 129.4, 128.7, 127.4,
117.9, 93.5, 85.3; IR (KBr) 2922, 2852, 2100, 1743, 1446, 1330, 1161,
1036, 850 cm−1; HRMS calcd [C14H10O2S + Na]+ 265.0299, found
265.0298.
(E)-1-Methyl-4-(styrylsulfonyl)benzene (3ac).3g The title com-
pound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a colorless solid: 81% yield
(E)-1,2,3-Trimethoxy-5-(2-(phenylsulfonyl)vinyl)benzene (3s).3i
The title compound was prepared according to the general working
procedure and purified by column chromatography (petroleum ether/
ethyl acetate = 10:1) to give the product as a colorless solid: 69% yield
(115.2 mg); mp = 143−144 °C; 1H NMR (CDCl3, 400 MHz) δ 7.97−
7.95 (m, 2H), 7.65−7.54 (m, 4H), 6.79 (d, J = 15.3 Hz, 1H), 6.72 (s,
2H), 3.873 (s, 3H), 3.869 (s, 6H); 13C NMR (CDCl3, 100 MHz) δ
153.5, 142.6, 140.8, 133.4, 129.4, 127.7, 127.6, 126.3, 105.8, 61.0, 56.2;
IR (KBr) 3048, 2942, 2841, 1579, 1506, 1421, 1280, 1254, 1127, 1081
cm−1; HRMS calcd [C17H18O5S + Na]+ 357.0773, found 357.0769.
1
(103.9 mg); mp = 117−118 °C; H NMR (CDCl3, 400 MHz) δ
7.83(d, J = 8.2 Hz, 2H), 7.66 (d, J = 15.4 Hz, 1 H), 7.49−7.46 (m,
2H), 7.41−7.35 (m, 3H), 7.34(d, J = 8.3 Hz, 2H), 6.85(d, J = 15.4 Hz,
1H), 2.43 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 144.4, 141.9,
137.8, 132.5, 131.1, 130.0, 129.1, 128.5, 127.7, 127.6. 21.6; IR (KBr)
3045, 2921, 2851, 1613, 1595, 1449, 1302, 1140, 1084 cm−1; HRMS
calcd [C15H14O2S + Na]+ 281.0612, found 281.0611.
4881
DOI: 10.1021/acs.joc.6b00661
J. Org. Chem. 2016, 81, 4876−4882

The Journal of Organic Chemistry
Note
(E)-1-Chloro-4-(styrylsulfonyl)benzene (3ad).3g The title com-
pound was prepared according to the general working procedure
and purified by column chromatography (petroleum ether/ethyl
acetate = 10:1) to give the product as a colorless solid: 40% yield (55.0
mg); mp = 78−80 °C; 1H NMR (CDCl3, 400 MHz) δ 7.90−7.87 (m,
2H), 7.69 (d, J = 15.4 Hz, 1H), 7.54−7.48 (m, 4H), 7.44−7.38 (m,
3H), 6.84 (d, J = 15.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 143.1,
140.1, 139.2, 132.2, 131.4, 129.7, 129.2, 128.6, 126.8; IR (KBr) 3061,
3039, 1610, 1575, 1473, 1449, 1394, 1309, 1278, 1142, 1083 cm−1;
HRMS calcd [C14H11ClO2S + Na]+ 301.0066, found 301.0064.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.joc.6b00661.
■
(5) (a) Xu, H. C.; Moeller, K. D. J. Am. Chem. Soc. 2010, 132, 2839.
(b) Huang, J. M.; Wang, X. X.; Dong, Y. Angew. Chem., Int. Ed. 2011,
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S
1H NMR and 13C NMR spectra for all products (PDF)
AUTHOR INFORMATION
Corresponding Authors
*Fax: 86-551-3631760. E-mail: zgzha@ustc.edu.cn.
*Fax: 86-551-3631760. E-mail: zwang3@ustc.edu.cn.
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
Financial support from the National Natural Science
Foundation of China (91213303, 21172205, J1030412, and
21472177) is greatly acknowledged.
(7) Buettner, G. R. Free Radical Biol. Med. 1987, 3, 259−303.
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Am. Chem. Soc. 2013, 135, 11481. (b) Narasaka, K.; Mochizuki, T.;
Hayakawa, S. Chem. Lett. 1994, 1705. (c) Mochizuki, T.; Hayakawa, S.;
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