Synthesis of diaryl sulfides through C–H bond functionalization of arylamides with cobalt salt and elemental sulfur

Article abstract of DOI:10.1016/j.tetlet.2019.02.032

A cobalt(II)-mediated, highly chemoselective thioarylation reaction of arylamides with elemental sulfur was reported. This reaction led to the formation of various symmetric diaryl sulfides in yields of up to 65% under mild reaction conditions. A cobalt-sulfur radical process was proposed based on preliminary results and mechanistic studies.

Full text of DOI:10.1016/j.tetlet.2019.02.032

Accepted Manuscript
Synthesis of diaryl sulfides through C–H bond functionalization of arylamides
with cobalt salt and elemental sulfur
Jian-Ye Li, Jun Huang, Shi-Jin Zhang, Chunna Yao, Wen-Wu Sun, Bin Liu,
Yingbi Zhou, Bin Wu
PII:
S0040-4039(19)30164-9
https://doi.org/10.1016/j.tetlet.2019.02.032
TETL 50626
DOI:
Reference:
Tetrahedron Letters
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Revised Date:
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14 December 2018
25 January 2019
18 February 2019
Please cite this article as: Li, J-Y., Huang, J., Zhang, S-J., Yao, C., Sun, W-W., Liu, B., Zhou, Y., Wu, B., Synthesis
of diaryl sulfides through C–H bond functionalization of arylamides with cobalt salt and elemental sulfur,
Tetrahedron Letters (2019), doi: https://doi.org/10.1016/j.tetlet.2019.02.032
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Synthesis of Diaryl Sulfides through C-H
Bond Functionalization of Arylamides with
Cobalt Salt and Elemental Sulfur
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Jian-Ye Li, Jun Huang, Shi-Jin Zhang, Chunna Yao, Wen-Wu Sun, Bin Liu, Yingbi Zhou and Bin Wu

1
Tetrahedron Letters
Synthesis of diaryl sulfides through C–H bond functionalization of arylamides with
cobalt salt and elemental sulfur
Jian-Ye Li,a, d Jun Huang,b, d Shi-Jin Zhang,c Chunna Yao,a Wen-Wu Sun,a, * Bin Liu,b, * Yingbi Zhou,b, *
and Bin Wu a, *
a School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, China
b Cardiovascular Research Center, Shantou University Medical College, Shantou 515041, China
c Department of Pharmacy, The Second Clinical Medical College of North Sichuan Medical College, Sichuan 637000, China
d Jian-Ye Li and Jun Huang contributed equally.
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
A cobalt(II)-mediated, highly chemoselective thioarylation reaction of arylamides with
elemental sulfur was reported. This reaction led to the formation of various symmetric diaryl
sulfides in yields of up to 65% under mild reaction conditions. A cobalt-sulfur radical process
was proposed based on preliminary results and mechanistic studies.
Available online
2009 Elsevier Ltd. All rights reserved.
Keywords:
cobalt(II)-mediated
C-H bond activation
diaryl sulfides
thioarylation
alternative for the formation of CS bonds.4 Numerous methods
based on CH functionalization have been developed to make
various diaryl sulfides using Cu,5 Fe,6 Ni,7 Pd,8 Rh,9 Ru10 and
Ag11 metal sources and thiols and diaryl disulfides as sulfur
reagents. However, the direct functionalization of C(sp2)H
bonds to synthesize diaryl sulfides using cobalt salts has rarely
been studied. Recently, Glorius and coworkers developed a
thioarylation reaction of N-pyrimidyl indole via cobalt catalyzed
C(sp2)H bond activation.12 Herein, we report a cobalt(II)-
mediated CH functionalization of arylamides to prepare diaryl
sulfides with elemental sulfur as a sulfur source.
As some of the most important organic sulfur-containing
compounds, diaryl sulfides have been considered to have an
advantageous structure for use in many pharmaceuticals,
biologically active natural products and advanced materials.1 For
example, the core structures of AZD4407 1, 2, Zaltoprofen 3, 4,
chlorpromazine hydrochloride 5 and quetiapine 6 are diaryl
sulfides, that exhibit biological activities against cancer, HIV,
inflammation, asthma, mood disorders and schizophrenia.2
This project was based on our initial work. During our studies
on cobalt-mediated C(sp2)H functionalization of carboxamide
7a, we isolated a dimerization product 9a in 14% yield and two
cobalt-amide complexes.13 When the reaction was carried out
.
under the conditions of Co(OAc)2 4H2O (2 equiv) and K2CO3 (2
equiv) in DMSO at 110 Cfor 24 h, a very small amount of 8a
was obtained along with the production of 9a. The main
difference between 8a and 9a spectroscopically is seen in the
HRMS data. We envisioned that the origin of the sulfur atom in
the structure of 8a might be the reduction of the solvent dimethyl
sulfoxide. Once we added two equivalents of elemental sulfur
into the reaction system,14 the yield of 8a increased to 34%,
accompanied by 9a and recovered 7a in 4% and 24% yields,
respectively (entry 1, Table 1). Then, we explored the effect of
oxidants and bases on the reaction. The addition of an external
Figure 1. Diaryl sulfide-containing pharmaceuticals
Over the past few decades, significant progress has been made
in transition-metal-catalyzed or transition-metal-mediated cross
coupling of aryl halides and various sulfur-based partners to
synthesize diaryl sulfide compounds.3 Currently, transition-
metal-catalyzed or transition-metal-mediated thioarylation of
C(sp2)–H bonds is becoming an increasingly attractive
———
* Corresponding author. 2016027@mail.scuec.edu.cn; bliu0210@yahoo.com; yz_sumc@163.com; 2015084@ mail.scuec.edu.cn

2
Tetrahedron
oxidant decreased the production of 8a (details in the
NaHCO3/S8, the optimized conditions were determined to be a
.
supporting information). NaHCO3 has proven to be optimal
(entries 2-6, Table 1). Among the several cobalt salts tested in the
reaction, Co(OAc)2 4H2O gave the best yield (entries 7-11, Table
combination of Co(OAc)2 4H2O (0.9 equiv), NaHCO3 (4 equiv)
and S8 (4 equiv) in DMSO at 110 C under N2 for 48 h, affording
.
the desired product 8a in 59% yield (entry 19, Table 1).15
1). After extensive investigation of reaction conditions, including
.
.
the loading of Co(OAc)2 4H2O and the ratio of Co(OAc)2 4H2O/
Table 1. Optimization of the reaction conditions
Entry
Cobalt salt (equiv)
Base (equiv)
S8
Yield [%]
(equiv)
8a
9a
rsm 7a
.
1
2
3
4
5
6
7
8
Co(OAc)2 4H2O/0.5
K2CO3/2
Na2CO3/2
K3PO4/2
2
2
2
2
2
2
2
2
2
2
4
4
4
4
4
4
4
4
4
4
4
4
4
4
1
2
34
32
17
21
27
35
6
4
3
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
37
11
24
38
74
67
50
51
86
67
73
68
47
82
75
58
57
47
44
33
26
21
21
60
52
40
29
30
.
Co(OAc)2 4H2O/0.5
.
Co(OAc)2 4H2O/0.5
.
Co(OAc)2 4H2O/0.5
NaOH/2
.
Co(OAc)2 4H2O/0.5
KHCO3/2
NaHCO3/2
NaHCO3/2
NaHCO3/2
NaHCO3/2
NaHCO3/2
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/4
NaHCO3/1
NaHCO3/2
NaHCO3/3
NaHCO3/4
NaHCO3/4
.
Co(OAc)2 4H2O/0.5
Co(acac)3/0.5
CoCl2/0.5
CoBr2/0.5
CoI2/0.5
27
21
27
49
16
21
32
37
50
48
46
59
40
36
24
36
52
25
38
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
.
Co(OAc)2 4H2O/0.5
.
Co(OAc)2 4H2O/0.1
.
Co(OAc)2 4H2O/0.2
.
Co(OAc)2 4H2O/0.3
.
Co(OAc)2 4H2O/0.4
.
Co(OAc)2 4H2O/0.6
.
Co(OAc)2 4H2O/0.7
.
Co(OAc)2 4H2O/0.8
.
Co(OAc)2 4H2O/0.9
.
Co(OAc)2 4H2O/1.0
.
Co(OAc)2 4H2O/1.2
.
Co(OAc)2 4H2O/0.9
.
Co(OAc)2 4H2O/0.9
.
Co(OAc)2 4H2O/0.9
.
Co(OAc)2 4H2O/0.9
.
Co(OAc)2 4H2O/0.9
With the optimal conditions known, we explored the substrate
scope of the reaction. Generally, the efficiency of this cobalt-
mediated thioarylation reaction of a C(sp2)H bond is limited
(Table 2). A series of symmetric diaryl sulfides bearing electron-
withdrawing or electron-donating groups on the benzene ring
were obtained in moderate to low yields with some amount of
starting materials recovered. It was found that the electronic
properties and position of substituents on the benzene ring have a
substantial effect on the production of the corresponding diaryl
sulfides. For example, the yield of the para-methyl- substituted
compound 8c was higher than that of the more sterically-
hindered ortho-methyl-substituted product 8b. The production of
the para-methoxy-substituted 8f was two fold that of the meta-
methoxy-substituted 8e. Likely because of electronic and steric
effects, ortho-methoxy-substituted 8d was not formed. The
electron-withdrawing groups, such as F, Cl, Br, I and CF3 on the
benzene ring made the reaction proceed more readily (e.g., 8g-8k
vs 8e), and these groups also provided appropriate sites for
further manipulation. Furthermore, thiophene substrates 7l and
7m underwent the thioarylation reaction of the C(sp2)H bond to
afford diaryl sulfides 8l and 8m in 24% and 52% yields,
respectively. Interestingly, more conjugated systems, such as the
dibenzofuran substrate 7n, provided more structurally
a
complicated product 8n in 34% yield. The structures of the
products were further confirmed by single-crystal X-ray
diffraction of 8a. The cross coupling of substrates 7e and 7k with
elemental sulfur under standard conditions afforded
heterocoupling product 8o in 32% yield and homocoupling
products 8e and 8k in 18% and 26% yields, respectively (eq. 1).
Figure 2. ORTEP Molecular Diagram of 8a

3
Table 2. Substrate scope a
Scheme 1. Control experiments for mechanistic study
In 2003, Solomon and Karlin reported the synthesis of the
copper-disulfide complex [(TMPA)Cu-S-S-Cu(TMPA)]2+ from
the reaction of [(TMPA)CuI(CH3CN)]+ with elemental sulfur.17
The structure of the copper-disulfide complex was confirmed by
single crystal X-ray diffraction (eq. 8). Inspired by this elegant
work, we tried to isolate cobalt-disulfide complex A, but failed.
In this period, we found that when S8 was added to the solution
of Co(OAc)2 in DMSO at 110 C under N2, the color of the
reaction mixture changed from purple to black, indicating that an
oxidation reaction might happen to cobalt(II) salt.
a
Typical reaction conditions: substrate (0.10 mmol),Co(OAc)2·4H2O (0.09
mmol), NaHCO3 (0.4 mmol), S8 (0.4 mmol) in DMSO (2.0 mL) under
o
b
Nitrogen at 110 C for 48 h. Isolated yields. Co(OAc)2·4H2O (0.06 mmol)
was used. c Co(OAc)2·4H2O (0.06 mmol) and Na2CO3 (0.4 mmol) were used.
To determine the mechanism of this reaction, several control
experiments were carried out (Scheme 1). First, the radical
scavenger reagent TEMPO was subjected to standard reaction
conditions. The production of 8a was decreased to a low yield
(eq. 2). Thiophenol substrate 11 was synthesized via three
consequent steps from commercially available diaryl disulfide
10.16 Then, the cobalt-mediated thioarylation reaction was carried
out under standard conditions with 11. Interestingly, another type
of diaryl sulfide, 12, was formed in 14% yield, for which the
coupling reaction occurred at the 5-position of the quinoline
backbone (eq. 4). In contrast, the reaction did not occur in the
absence of elemental sulfur. When equal amounts of 11 and 7a
were subjected to standard conditions, 12 was obtained in 7%
yield along with a small amount of complicated mixtures (eq. 6).
Similarly, the reaction did not proceed without elemental sulfur.
These results indicated that this reaction probably experienced a
free radical-involving process and that elemental sulfur had a key
effect on the reaction.
Based on these results and literature work, a possible
mechanism for this reaction is depicted in Scheme 2. Co(OAc)2 is
oxidized by elemental sulfur to form cobalt(III)-disulfide
complex A, which undergoes ligand exchange with 7a and then
C(sp2)H bond activation to afford disulfide intermediate B. B
coordinates with another molecule of 7a and undergoes
homolysis to form sulfur radical species C,18 which provides D
through a radical addition reaction. Rearomatization of D leads to
the formation of E. E undergoes reductive elimination and
hydrolysis to afford product 8a.
In conclusion, we have studied the thioarylation reaction of
arylamide via cobalt(II)-mediated C(sp2)H bond activation. This
method provides a straightforward synthesis of symmetric diaryl
sulfides with high chemoselectivity, albeit in moderate yields.
Extensive investigation showed that the cooperation of three
components (Co(OAc)2, NaHCO3 and elemental sulfur) is

4
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Supplementary Material
Highlights
A cobalt(II)-mediated, highly chemoselective
thioarylation reaction of arylamides with elemental
sulfur was reported.
This reaction led to the formation of various
symmetric diaryl sulfides in yields of up to 65%
under mild reaction conditions.
A cobalt-sulfur radical process was proposed.
Graphical Abstract
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Synthesis of Diaryl Sulfides through C-H
Bond Functionalization of Arylamides with
Cobalt Salt and Elemental Sulfur
Leave this area blank for abstract info.
Jian-Ye Li, Jun Huang, Shi-Jin Zhang, Chunna Yao, Wen-Wu Sun, Bin Liu, Yingbi Zhou and Bin Wu