Synthesis of diaryl sulfides based on copper-doped OMS-2

Article abstract of DOI:10.1177/1747519820966985

We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material can be recycled several times.

Full text of DOI:10.1177/1747519820966985

966985CHL0010.1177/1747519820966985Journal of Chemical ResearchY
u
et al.
research-article2020
Research Paper
Journal of Chemical Research
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Synthesis of diaryl sulfides based on
copper-doped OMS-2
https://doi.org/10.1177/1747519820966985
DOI: 10.1177/1747519820966985
journals.sagepub.com/home/chl
Shao-Qiang Yu1,2, Na Liu1,2, Ming-Guo Liu1,2 and Long Wang1,2
Abstract
We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst.
Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the
C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental
friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material
can be recycled several times.
Keywords
C–S coupling, diaryl sulfide, environmental friendliness, green chemistry, heterogeneous catalysis
Date received: 25 July 2020; accepted: 28 September 2020
I
SH
S
Cu-OMS-2
R1
R2
R1
R2
New catalytic materials: Cu-OMS-2
-
-Cu-OMS-2: green, efficient and reusable
Mild conditions, external ligand-free and lower temperature
-
carried out in air without N2 protection. Compared with
traditional methods, the transition metal–catalyzed cou-
pling reaction of halogenated hydrocarbons and sulfur
compounds has the advantages of simple operation, high
efficiency, low cost, and mild reaction conditions, which
have firmly attracted the attention of researchers. In 2012,
Das and Chakraborty8 revealed a method to synthesize
thioethers using thiophenol and organic boric acid as
Introduction
Sulfides, appearing frequently in natural products and med-
icines,1,2 are critical sulfur-containing organic compounds,
especially in the field of new synthetic drugs. However, the
traditional method of synthesizing sulfides by transition
metal–catalyzed C–S coupling reaction of aryl halides with
thiols has the shortcomings of high cost, harsh reaction
conditions, and long response times.3–5 Therefore, it is nec-
essary to develop new and efficient synthetic methods by
taking advantage of new catalytic materials.
1Hubei Key Laboratory of Natural Products Research and Development,
China Three Gorges University, College of Biological and
Pharmaceutical Science, Yichang, P.R. China
In 1978, a C–S bond coupling reaction catalyzed by
palladium was reported by Kosugi et al.6, who used
Pd(PPh3)4 as the catalyst to produce a series of thioether
compounds by coupling iodobenzene or bromobenzene
compounds with thiophenols or mercaptans. In 2009, Xu
et al.7 reported a method to construct C–S bonds using
halogenated hydrocarbons and mercaptans with Cu2O.
The main advantages of this method were that cheap and
readily available Cu2O replaced the expensive and spe-
cialized copper salts, and that the reaction could be
2Key Laboratory of Inorganic Nonmetallic Crystalline and Energy
Conversion Materials, College of Materials and Chemical Engineering,
China Three Gorges University, Yichang, P.R. China
Corresponding author:
Long Wang, Key Laboratory of Inorganic Nonmetallic Crystalline
and Energy Conversion Materials, College of Materials and Chemical
Engineering, China Three Gorges University, Yichang, P.R. China.
Email: wanglongchem@ctgu.edu.cn
Creative Commons Non Commercial CC BY-NC: This article is distributed under the terms of the Creative Commons
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Open Access pages (https://us.sagepub.com/en-us/nam/open-access-at-sage).

2
Journal of Chemical Research 00(0)
(a)
R1
AgOTf (1.5 equiv)
KOH (3 equiv)
S
SH
SH
B(OH)2
R2
R1
R2
C
DMF, N2, 150 °
4 Å Molecular Sieves
(b)
R1
FeCl 6H O
34
L Prolin2e
I
S
ꢀ
R2
R1
R2
KOH (2 equiv)
TBAB, 24 h,130 °
C
(c)
R1
I
SH
S
Cu-OMS-2, DMSO
R2
R1
R2
C
°
Cs2CO3 air, 6 h, 95
,
Mild conditions, external ligand-free, lower temperature
New catalytic material: Cu-OMS-2
Cu-OMS-2: green, efficient and reusable
Scheme 1. Strategies for the construction of sulfides: (a) Das and Chakraborty,8 (b) Anilkumar (2015)9, and (c) this work.
substrates with AgOTf, 4Å molecular sieves, and KOH
(Scheme 1(a)). In 2015, Anilkumar who has devoted sig-
nificant efforts to study transition metal–catalyzed cou-
pling reactions to prepare sulfides9–11 reported a method to
produce sulfides using an Fe salt as the catalyst (Scheme
1(b)). We have also reported some methods for synthesiz-
ing aryl sulfides by heterogeneous catalysis.12–14
Manganese oxide octahedral molecular sieves (OMS-2),
the structure of which is similar to zeolite molecular sieves,
are a new type of material that can supply a high specific
surface area. Furthermore, the specialized framework struc-
ture of OMS-2 with a large number of mixed valence Mn
ions (Mn2+, Mn3+, Mn4+) allows it to perform well in redox
reactions. Later, researchers found that OMS-2 also dem-
onstrated an excellent performance in the field of organic
synthetic catalysis when different metal ions were used to
modify OMS. Reflux,15–18 ball milling,19 impregnation,20
Figure 1. X-ray powder diffractogram of Cu–OMS-2.
and multi-step hydrothermal methods21–23 can produce
OMS doped with Cu.
Based on our previous research,26–32 herein, we report a
Finally, a one-step hydrothermal method was developed
method to efficiently synthesize diaryl sulfide compounds
by utilizing copper-doped manganese oxide octahedral
molecular sieves (Cu–OMS-2) to catalyze the heterogene-
ous C–S coupling reaction of thiophenols and aryl halides
(Scheme 1(c)).
to synthesize the copper-doped manganese oxide octahedral
molecular sieves (Cu–OMS-2). Figure 1 illustrates that the
synthesized Cu–OMS-2 catalyst has a typical cryptomelane
structure (KMn8O16).24,25 Obvious characteristic peaks
observed at the angles of 12.6°, 17.9°, 28.7°, 37.5°, 41.9°,
49.9°, and 60.1° are basically consistent with the data for
standard OMS-2 PDF card (JCPDS-29-1020). Furthermore,
the image indicates that Cu did not affect the crystal bulk
structure of OMS-2 in the prepared Cu–OMS-2 catalyst. In
addition, no obvious characteristic diffraction peaks corre-
sponding to copper crystal phase oxides were detected in the
X-ray diffraction (XRD) pattern, implying that the doped
copper was highly dispersed in Cu–OMS-2. It is further
speculated that some copper ions are located into the frame-
work or pores. The morphology of the catalyst was observed
by scanning electron microscope (SEM). Figure 2 illustrates
the rod-like morphology of Cu–OMS-2.
Results and discussion
We began our initial trials with 4-methylthiophenol (1a) and
4-cyanoiodobenzene (2a) as model substrates for the con-
struction of C–S bond in the presence of Cu–OMS-2 as the
catalyst. We examined factors such as temperature, solvent,
and base, which influence the reaction and the results are
shown in Table 1. To our delight, the desired product 3a was
obtained in 47% yield at 60°C (Table 1, entry 1). Increasing
the temperature to 95°C (Table 1, entry 2), the yield reached
89%. Further increasing the temperature to 110°C did not

Yu et al.
3
Table 2. Scope of thiophenols and aryl iodobenzenes.a
I
SH
S
Cu-OMS-2
DMSO
R1
R2
R1
R2
Cs2CO3
,
1
2
3
Entry
Product
R1
R2
Yield (%)
1
2
3
4
5
6
7
8
3a
3b
3c
3d
3e
3f
3g
3h
3i
4-CH3
2-Cl
2-Cl
3-Cl
4-Cl
4-Cl
4-Cl
4-F
4-F
4-CH3
4-OCH3
2-OCH3
4-OCH3
4-CN
4-CN
4-NO2
4-CN
4-CN
4-NO2
4-COCH3
4-CN
4-NO2
4-NO2
4-CN
4-H
89
79
81
83
85
85
74
80
83
88
90
36
43
9
10
11
12
13
3j
3k
3l
Figure 2. SEM image of Cu–OMS-2.
3m
4-H
aReaction conditions: 1 (1mmol), 2 (1mmol), Cs2CO3 (2 equiv.),
Cu–OMS-2 (10mg), DMSO (2.5mL), 95°C, 6h.
Table 1. Reaction optimization.a
I
S
SH
Cu-OMS-2
run in 95°C without Cu–OMS-2, the yield of the target
product was reduced to 36% (Table 1, entry 14). It is note-
worthy that Cu–OMS-2 greatly improved the yield and
played an indispensable role during the reaction process.
Thus, 4-methylthiophenol and 4-cyanoiodobenzene as the
substrates with Cs2CO3 as the base and Cu–OMS-2 as the
catalyst in DMSO at 95°C were determined to be the opti-
mal reaction conditions.
Base, solvent
CN
CN
1a
3a
2a
Entry
Base
Solvent
Temp (°C)
Yieldb (%)
1
Cs2CO3
Cs2CO3
Cs2CO3
Na2CO3
K2CO3
LiOH
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
THF
toluene
DMF
DMSO
DMSO
DMSO
60
95
110
95
95
95
95
95
95
95
95
95
95
95
47
89
88
21
29
17
84
81
0
2f
3
4
5
6
7
8
9
10
11
12c
13d
14e
With the optimal reaction conditions having been estab-
lished, we next focused on investigating the scope of sub-
strates. So as to synthesize diaryl sulfide products, different
aryl iodides and substituted thiophenols were reacted under
the optimal conditions (Table 2). We succeeded in prepar-
ing various C–S coupling products with high yields ranging
74%–90%. Moreover, fluorine- or chlorine-substituted
thiophenols can react with aryl iodides to afford the target
products (3b–i) in high yields. The yield of the target prod-
uct obtained from methyl-substituted thiophenol was higher
than that of fluorine- or chlorine-substituted thiophenols. In
addition, when we used substituted thiophenols in reactions
with iodobenzenes with no electron-withdrawing group at
the para position, the reactions proceeded smoothly to give
the corresponding thioether products (3l and 3m) under the
optimized conditions; however, the yields were lower.
Furthermore, recycling studies using Cu–OMS-2 were
investigated by operating the reaction under the optimized
conditions (Scheme 2). We can clearly see that recycled
Cu–OMS-2 worked well and gave an excellent yield of
86% of the diaryl sulfide compound after six recycles. In
addition, the results indicate that Cu–OMS-2 is stable over
several cycles.
NaOH
KOH
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
0
67
48
87
36
aReaction conditions: 4-methylthiophenol (1mmol), 4-cyanoiodobenzene
(1mmol), base (2mmol), Cu–OMS-2 (10mg), solvent (2.5mL), 95°C, 6h.
bIsolated yield.
cCu–OMS-2 (5mg).
dCu–OMS-2 (16mg).
eNo Cu–OMS-2, 95°C.
fThe optimal reaction condition.
improve the yield (Table 1, entry 3). Therefore, a tempera-
ture of 95°C was optimal for this reaction. Among the
screened bases, Cs2CO3 was clearly superior to other bases.
NaOH, KOH, and Cs2CO3 are more compatible with this
reaction compared to Na2CO3 or K2CO3, with Cs2CO3 giv-
ing the highest yield of 89% (Table 1, entries 4–8). Solvent
screening revealed that DMSO was found to be the best sol-
vent. DMF was suitable for this reaction, albeit providing a
lower yield of 67%. However, the reaction failed to give the
desired product when THF or toluene was used as the sol-
Conclusion
vent (Table 1, entries 9–11). It is not obvious that the reac- In conclusion, we have described a practical protocol for
tion could be improved or inhibited by increasing or efficiently preparing diaryl sulfides using Cu–OMS-2 to
decreasing the amount of catalyst. When the reaction was catalyze
the
C–S
coupling
reactions
of

4
Journal of Chemical Research 00(0)
removing the solvent, the resulting crude residue was puri-
fied by column chromatography with pure petroleum as the
eluent to give compound 3.
S
I
SH
Cu-OMS-2, 95 °C
Cs CO
3, DMSO, 6 h
CN
CN
2
1a
2a
3a
4-(p-Tolylthio)benzonitrile (3a). Yield: 89%, white solid,
m.p. 95-96°C (lit.33); 1H NMR (400 MHz, CDCl3): δ: 7.40-
7.32 (m, 4H, Ar-H), 7.18 (d, J = 8.4 Hz, 2H, Ar-H), 7.04 (d,
J = 8.4 Hz, 2H, Ar-H), 2.3 (s, 3H, CH3); 13C NMR (101
MHz, CDCl3): δ: 146.65, 140.01, 135.01, 132.32, 130.80,
126.78, 126.69, 118.97, 108.28, 21.37.
4-[(2-Chlorophenyl)thio]benzonitrile (3b). Yield: 79%, color-
less oily liquid; 1H NMR (400 MHz, CDCl3): δ: 7.49-7.42
(m, 4H, Ar-H), 7.34-7.28 (m, 1H, Ar-H), 7.26-7.20 (m,1H,
Ar-H), 7.12 (d, J=8.8 Hz, 2H, Ar-H); 13C NMR (101 MHz,
CDCl3): δ: 143.19, 138.14, 135.87, 132.61, 130.75, 130.73,
130.56, 128.17, 127.94, 118.71, 109.49.
Scheme 2. Catalyst recycling studies.
(2-Chlorophenyl)(4-nitrophenyl) sulfane (3c). Yield: 81%,
yellow solid, m.p. 111-113°C; 1H NMR (400 MHz,
CDCl3): δ: 8.10 (d, J=7.2 Hz, 2H, Ar-H), 7.57 (t, J=6.4
Hz, 2H, Ar-H), 7.41 (t, J=6.0 Hz, 1H, Ar-H), 7.33 (t, J=6.0
Hz, 1H, Ar-H), 7.20 (d, J=6.8 Hz, 2H, Ar-H); 13C NMR
(101 MHz, CDCl3): δ: 145.92, 145.85, 138.54, 136.32,
131.06, 130.84, 130.11, 128.01, 127.45, 124.21.
substituted thiophenols and aryl halides. This protocol has
the advantages of environmental friendliness, simple oper-
ation, high yields, good tolerance of functional groups, and
the Cu–OMS-2 catalyst material can be recycled several
times.
General experiments
4-[(3-Chlorophenyl)thio]benzonitrile (3d). Yield: 83%, color-
less oily liquid; H NMR (400 MHz, CDCl3): δ: 7.45 (d,
J =8.8 Hz, 2H, Ar-H), 7.40 (s, 1H, Ar-H), 7.34-7.25 (m,
3H, Ar-H), 7.16 (d, J=8.8 Hz, 2H, Ar-H); 13C NMR (101
MHz, CDCl3): δ: 144.11, 135.49, 133.45, 132.64, 131.88,
130.91, 130.64, 129.38, 128.29, 118.63, 109.58.
1
1
All the obtained products were characterized by H NMR
and 13C NMR spectroscopy (400 or 100MHz). Chemical
shifts are reported in parts per million (ppm, δ) downfield
from tetramethylsilane. Proton coupling patterns are
described as singlet (s), doublet (d), triplet (t), and multiplet
(m); TLC was performed using commercially prepared
100–400 mesh silica gel plates (GF 254), and visualization
was effected at 254nm; all the reagents were purchased
from commercial sources and were used without further
purification.
4-[(4-Chlorophenyl)thio]benzonitrile (3e). Yield: 85%, white
1
solid, m.p. 88-89°C (lit.34); H NMR (400 MHz, CDCl3):
δ: 7.51 (d, J=8.8 Hz, 2H, Ar-H), 7.46-7.39 (m, 4H, Ar-H),
7.18 (d, J=8.8 Hz, 2H, Ar-H); 13C NMR (101 MHz,
CDCl3): δ: 144.88, 135.71, 135.53, 132.47, 130.12, 129.49,
127.51, 118.56, 109.12.
Preparation of Cu–OMS-2
(4-Chlorophenyl)(4-nitrophenyl)sulfane (3f). Yield: 85%, yel-
Manganese sulfate (8.8g) and Cu(NO3)2·3H2O (0.6375g)
in purified water (100mL) were added to a solution of puri-
fied water (30mL) containing concentrated nitric acid
(3mL) and potassium permanganate (5.89g). The mixed
solution was placed in an oven at 100°C for the hydrother-
mal reaction for 24h. The product was then filtered,
washed, and dried at 120°C for 8h. Finally, the dry Cu–
OMS-2 was calcined in a muffle furnace at 350°C for 2h to
afford a black powder.
1
low solid, m.p. 89-90°C (lit.35); H NMR (400 MHz,
CDCl3): δ: 8.10-8.06 (m, 2H, Ar-H), 7.50-7.41 (m, 4H,
Ar-H), 7.22-7.16 (m, 2H, Ar-H); 13C NMR (101 MHz,
CDCl3): δ: 147.66, 145.64,136.10, 135.90, 130.32, 129.16,
126.97, 124.20.
1-[4-((4-Chlorophenyl)thio)phenyl]ethan-1-one (3g). Yield:
74%, white solid, m.p. 83-84°C (lit.34); 1H NMR (400 MHz,
CDCl3): δ: 7.48 (d, J=8 Hz, 2H, Ar-H), 7.42-7.35 (m, 4H,
Ar-H), 7.22 (d, J=8 Hz, 2H, Ar-H), 2.56 (s, 3H, CH3); 13
C
Typical procedure for the synthesis of 3
NMR (101 MHz, CDCl3): δ: 197.11, 144.06, 135.03, 134.90,
134.84, 130.95, 129.92, 129.04, 127.83, 26.53.
Benzenethiol 1 (1mmol) was added to Schlenk tube with
DMSO (2.5mL) under oxygen at room temperature.
Subsequently, Cs2CO3 (2.0mmol), Cu–OMS-2 (10mg),
and substituted iodobenzene 2 (1mmol) were added to the
Schlenk tube quickly. The mixture was heated at 95°C for
6h. After the reaction was completed, the mixture was
cooled to room temperature. Water (10mL) was added to
the mixture, and the crude was extracted with CH2Cl2. After
4-[(4-Fluorophenyl)thio]benzonitrile (3h). Yield: 80%, white
1
solid, m.p. 85-86°C (lit.33); H NMR (400 MHz, CDCl3):
δ: 7.54-7.50 (m, 2H, Ar-H), 7.48 (d, J=6.8 Hz, 2H, Ar-H),
7.17-7.10 (m, 4H, Ar-H); 13C NMR (101 MHz, CDCl3): δ:
164.58, 162.58, 145.83, 137.07, 132.43, 126.88, 125.84,
118.71, 117.34, 108.81.

Yu et al.
5
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2H, Ar-H), 7.12-7.05 (m, 4H, Ar-H); 13C NMR (101 MHz,
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1
white solid, m.p. 92-93°C (lit.33); H NMR (400 MHz,
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Ar-H), 6.97 (d, J=8 Hz, 2H, Ar-H), 3.86 (s, 3H, OCH3);
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5H, Ar-H), 7.23-7.21 (m, 1H, Ar-H), 7.09-7.07 (m, 1H,
Ar-H), 6.91-6.85 (m, 2H, Ar-H), 3.87 (s, 3H, OCH3); 13C
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The author(s) declared no potential conflicts of interest with respect
to the research, authorship, and/or publication of this article.
Funding
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The author(s) disclosed receipt of the following financial support
for the research, authorship, and/or publication of this article: The
authors gratefully acknowledge financial support of this work by
the National Natural Science Foundation of China (21602123)
and the 111 Project (no. D20015).
ORCID iD
33. Wang Y, Deng LL, Wang XC, et al. ACS Catal 2019; 9:
1630.
Long Wang
https://orcid.org/0000-0001-7548-014X
34. Yao F, Zhang RL, Wu YC, et al. J Chem Res 2015; 39:
612.
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