Forging C?S(Se) Bonds by Nickel-catalyzed Decarbonylation of Carboxylic Acid and Cleavage of Aryl Dichalcogenides

Article abstract of DOI:10.1002/ejoc.202100115

A nickel-catalyzed decarbonylation of carboxylic acids cross-coupling protocol has been developed for the straightforward C?S(Se) bond formation. This reaction is promoted by a commercially-available, user-friendly, inexpensive, air and moisture-stable nickel precatalyst. Various carboxylic acids and a wide range of aryl dichalcogenide substrates were tolerated in this process which afforded products in good to excellent yields. In addition, the present reaction can be conducted on gram scale in good yield.

Full text of DOI:10.1002/ejoc.202100115

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Forging CÀ S(Se) Bonds by Nickel-catalyzed
Decarbonylation of Carboxylic Acid and Cleavage of Aryl
Dichalcogenides
Jing-Ya Zhou[a] and Yong-Ming Zhu*[a]
A nickel-catalyzed decarbonylation of carboxylic acids cross-
coupling protocol has been developed for the straightforward
CÀ S(Se) bond formation. This reaction is promoted by a
commercially-available, user-friendly, inexpensive, air and mois-
ture-stable nickel precatalyst. Various carboxylic acids and a
wide range of aryl dichalcogenide substrates were tolerated in
this process which afforded products in good to excellent
yields. In addition, the present reaction can be conducted on
gram scale in good yield.
Introduction
Aryl chalcogen-containing compounds are of much importance
and continued interest because of their essential applications in
biologically active molecules,[1] pharmaceuticals[2] and organic
materials[3] (Figure 1). Examples include Vortioxetine (an anti-
depressant
drug),
Chloropromazine
(a
dopamine
antagonist),[2a,b] Thymitaq (an anticancer)[2d] and organic elec-
tronic material triselenasumanene.[3b] Therefore, methods for
effectively constructing CÀ S(Se) bonds continue to attract
attention. The common synthetic methods for the synthesis of
aryl sulfides use transition metal-catalyzed cross-coupling of
aryl halides or pseudohalides with thiols.[4] However, dimeriza-
tion of thiols or selenols is a major obstacle for CÀ S(Se) bond
formation.[5]
Figure 1. Examples of pharmaceutically-relevant thioethers
In the last few decades, chemists are more and more
interested in nickel catalysis. This is because it has the proper-
ties of easier oxidative addition,[6a] abundance and economic
advantages.[6b] In particular, the nickel-catalyzed decarbonyla-
tion reaction has been extensively explored by various research
groups.[7,8] For instance (Scheme 1), in 2018, Szostak’s research
group reported the use of air and moisture-stable nickel
precatalysts to convert thioesters into thioethers by
decarbonylation.[9] In the same year, Rueping’s research group
disclosed a new and selective cross-coupling reaction of esters
and amides with mercaptans as coupling partners.[10] In 2019,
our laboratory reported that under the catalysis of a stable
nickel precatalyst, anhydride and thiophenol established CÀ S
bonds through decarbonylation or decarbonylation followed by
decarboxylation.[11] Most recently, Sanford et al. described the
development of a nickel-catalyzed decarbonylative reaction for
the synthesis of fluoroalkyl thioethers from the corresponding
thioesters.[12] Many additional reports about nickel-catalyzed
cross-electrophilic coupling reactions have been reported.[13] In
order for metal catalysis to be widely used in industrial research,
it is still urgent to find robust, bench-stable Ni(II) precatalysts.
Carboxylic acids are one of the most attractive chemical
components in organic synthesis and one of the most common
organic molecules in nature.[14] The development of thioethers
through cross-coupling of readily accessible carboxylic acids
would greatly expand the range of electrophiles, given that: a)
carboxylic acids are inexpensive and readily available; b)
carboxylic acids are derived from a different pool of precursors
than aryl halides and pseudohalides; and c) carboxylic acids can
be used directly as starting materials for the reaction, or they
can be converted into carboxylic acid derivatives under mild
reaction conditions to participate in the reaction.[15]
[a] J.-Y. Zhou, Prof. Y.-M. Zhu
Herein, we report the nickel-catalyzed decarbonylation
cross-coupling reaction of carboxylic acids and aryl dichalcoge-
nides (Scheme 1c).
College of Pharmaceutical Sciences
Soochow University
Suzhou 215123, China
E-mail: zhuyongming@suda.edu.cn
http://pharm.suda.edu.cn/29/78/c11611a272760/page.htm
Supporting information for this article is available on the WWW under
https://doi.org/10.1002/ejoc.202100115
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Therefore, we screened the ratio of Zn and Mn and found that
when Mn:Zn=2:1.5, the yield increased slightly to 75%
(entry 17–20). Notably, increasing the dppp loading to 40 mol%
afforded the product 3a in 80% yield (entry 21). When no metal
was added or only Mn was added in the reaction system, there
was no or little decarbonylation product, but thioester was
formed (entry 22–23). When only Zn was added, 3a was
obtained with 45% yield (entry 24). In the absence of Piv2O,
only 34% yield of the expected product was formed (entry 25).
This suggests that part of the carboxylic acid is obtained
through the formation of thioester intermediates, and then
decarbonylates to the target product. As anticipated, control
experiments revealed that the transformation did not proceed
without the nickel catalyst or in the absence of supporting
ligand (entry 26–27).
Encouraged by the initial results, we used 2-naphthoic acid
as the coupling partner to explore the flexibility of various
symmetric disulfides (Table 2). The disulfides with both elec-
tron-rich or electron-poor groups can be converted into aryl
sulfides smoothly. Aryl disulfides with an electron-donating
group or an electron withdrawing group on the benzene ring
furnished the expected coupling products 3a–3i in 76–92%
yields. In addition, steric hindrance doesn’t have much influence
on the reaction, and the target compounds with good to
excellent yields can be achieved (3e, 3h). Unsubstituted aryl
sulfide can also provide cross-coupling product in high yield
(3j). Very encouragingly, aliphatic disulfide compounds were
also workable, providing desired cross-coupling compounds in
moderate yields (3k, 3l).
Scheme 1. Metal-catalyzed decarbonylation coupling reaction
Results and Discussion
At the outset, 2-naphthoic acid (1 equiv.) and 1,2-bis(4-
chlorophenyl)disulfane (1.2 equiv.) were chosen as coupling
partners in the presence of a nickel/ligand catalytic system with
the use of additives (Table 1). We first screened several catalysts
using toluene as the solvent. With NiBr2(DME) (10 mol%) as the
catalyst, different phosphorus ligands were screened (entry 1–
3). Although there is no target thioether formed, part of the
thioester is formed under the action of the bidentate phosphine
ligand. Switching bases to NaHCO3 or K2CO3 resulted in no
decarbonylation products (entry 4–5). To our delight, changing
the metal species to Zn provided 15% yield of 3a (entry 6), but
replacing Zn with Mg led to no desired product (entry 7). We
next turned our attention to nickel precatalysts and found that
the more stable and less expensive nickel precatalysts Ni(dppp)
Cl2 can provide the thioether product with a yield of 25%.
Other air-stable nickel sources such as NiCl2, Ni(OAc)·4H2O and
NiBr2, resulted in reduced yield compared to the Ni(dppp)Cl2
(entry 8–11). When adding pivalic anhydride in the presence of
a base, the target compound is not obtained (entry 12). Further
optimizations were performed by screening various anhydrides.
The results showed that the use of Piv2O increased the yield to
55% (entry 13–14). When the amount of Piv2O was increased to
1.5 equiv., the yield of the target product was increased to 62%
(entry 15). Encouraged by the results of this reaction conditions,
and inspired by the fact that only thioesters were generated by
the addition of Mn, we tried to add Zn and Mn at the same
time. Interestingly, by adding Zn and Mn at the same time, the
yield of the desired product was increased to 71% (entry 16).
We subsequently turned our attention to a series of
carboxylic acids to determine the scope of our method
(Table 3). As shown, the scope of the reaction is very broad and
tolerates the coupling of electron-neutral, electron-withdrawing
and electron-rich substrates. phenyl, naphthyl, halogen, hydro-
carbyl, methoxy, cyano were all well tolerated in this reaction
(4a–4r, 4u). Acetyl group and ester group also performed well
(4s, 4t). This reaction is also workable to cinnamic acid, with an
83% yield obtained (4v). To our delight, most heterocycles are
suitable for this reaction. Except for the product 4x, most of the
heterocycles can give moderate to good decarbonylation cross-
coupling compounds (4w, 4y–4ad). In addition, steric hin-
drance has a slight impact on yield (4e, 4f). To apply our
discovery to medicinal chemistry and pharmaceutical research,
we carried out direct derivatization of a drug. Adapalene
(Retinoic acid drug) was cross-coupled with diphenyl disulfide
to obtain compound 4ae with a yield of 76% (4ae). Despite the
broad scope in the aforementioned examples, however,
aliphatic carboxylic acids are not suitable for this reaction (4af).
To further demonstrate the potential of this method, we
investigated reactions between carboxylic acids and diselenides
(Table 4). When diselenide reacts with different naphthoic acid,
a moderate to good yield can be obtained (5a–5c). Benzoic
acids with different substituent can also provide cross-coupling
products in moderate yields (5e–5h). For example, 4-phenyl-
benzoic acid can provide the target product with a yield of 40%
(5d).
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Table 1. Optimization of the reaction conditions.[a,b]
Entry
Catalyst
Ligand
Metal
Additive
Base
Yield
3a
3a’
1
2
3
4
5
6
7
8
NiBr2(DME)
NiBr2(DME)
NiBr2(DME)
NiBr2(DME)
NiBr2(DME)
NiBr2(DME)
NiBr2(DME)
NiCl2
PPh3
Mn
Mn
Mn
Mn
Mn
Zn
Mg
Zn
Zn
Zn
Zn
Zn
Zn
Zn
Zn
/
/
/
/
/
/
/
/
Na2CO3
Na2CO3
Na2CO3
NaHCO3
K2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
Na2CO3
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
none
none
none
none
none
15%
none
none
25%
trace
20%
none
55%
34%
62%
71%
75%
74%
71%
59%
80%
none
trace
45%
34%
none
none
/
dppb
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
dppp
/
48%
49%
20%
/
/
/
/
/
/
/
/
/
/
/
/
/
9
10
11
Ni(dppp)Cl2
Ni(OAc)·4H2O
NiBr2
/
/
/
12[c]
13[c]
14[c]
15[d]
16[d]
17[d]
18[d]
19[d]
20[d]
21[d,e]
22[d,e]
23[d,e,f]
24[d,e,g]
25[e]
26[d,e]
27[d,e]
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
Ni(dppp)Cl2
/
Piv2O
Piv2O
CH3(CO)2O
Piv2O
Piv2O
Piv2O
Piv2O
Piv2O
Piv2O
Piv2O
Piv2O
Piv2O
Piv2O
/
Mn:Zn=1.5:1.5
Mn:Zn=2:1.5
Mn:Zn=2.5:1.5
Mn:Zn=2:2.5
Mn:Zn=2:2
Mn:Zn=2:1.5
/
/
/
/
/
84%
49%
/
/
/
/
Mn
Zn
Mn:Zn=2:1.5
Mn:Zn=2:1.5
Mn:Zn=2:1.5
Piv2O
Piv2O
Ni(dppp)Cl2
[a] Reaction conditions: 2-naphthoic acid (0.5 mmol), 1,2-bis(4-chlorophenyl)disulfane (0.6 mmol), catalyst (10 mol%), ligand (20 mol%), metal (1.25 mmol),
°
base (0.5 mmol) and toluene (2 mL), N2, 160 C, 24 h. [b] Isolated yields. [c] Anhydride (0.5 mmol). [d] Piv2O (0.75 mmol). [e] dppp (40 mol%) [f] Mn (1 mmol).
[g] Zn (0.75 mmol)
To prove the practicality of this method, we next performed
a gram-scale reaction of 2-naphthoic acid with 1,2-bis(4-meth-
oxyphenyl)disulfane. When the model reaction was performed
on a 6.0 mmol scale, the yield of the desired product 3f was
obtained in 74% (Scheme 2), thus demonstrating the scalability
of this strategy.
With the completion of the substrate expansion, we
performed some mechanism control experiments (Scheme 3). It
is reported in the literature that the combination of the
carboxylic acid and pivalic anhydride was effective for the
generation of the active mixed anhydride intermediate.[16]
Therefore, we synthesized the mixed anhydride according to
the relevant literature,[17] and under standard conditions, the
desired product was isolated with a yield of 70% (Scheme 3a).
In addition, in the absence of nickel source and pivalic
anhydride, we have separated a small amount of thioester
(Scheme 3b).
Based on the previous literature reports,[10,18] a plausible
mechanism of the Ni(II)-catalyzed decarbonylation cross-cou-
pling reaction of aryl dichalcogenides and carboxylic acids is
shown in Scheme 4. We speculate that there are two reaction
pathways. First, the carboxylic acid was activated in situ by
Piv2O to produce a mixing anhydride A, followed by oxidative
addition with the Ni(0) give an intermediate B. At the same
time, disulfide compound generated aryl thiolate ion under the
action of reducing reagent.[19] Intermediate B was attacked by
aryl thiolate ion to obtain compound E. The resulting E was
further decarbonylated to generate intermediate F, which is
then reductively eliminated to obtain the desired product. In
addition, building the CÀ S bond may pass through path B.
Carboxylic acid was attacked by aryl thiolate ion to form
thioester. The C (acyl)À S bond of thioester D is oxidatively
Scheme 2. Large-scale synthesis.
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Table 2. Substrate scope of disulfides.[a,b]
elimination to obtain target product and active Ni(0) to
complete the catalytic cycle.
Conclusion
In conclusion, we have developed a nickel-catalyzed decarbon-
ylative cross-coupling reaction of carboxylic acids and aryl
dichalcogenides. This method can be applied practically with a
wide range of substrates and good tolerance of functional
groups, compatible with ketone, ester, cyanide and alkene. In
this reaction carboxylic acid was used directly as the source of
aryl group to realize one-pot construction of CÀ S(Se) bonds. By
using this method, we can not only directly use low-odor and
low-sensitivity aryl dichalcogenides to construct CÀ S(Se) bonds,
but also make the reaction on gram scale with good yield.
Experimental Section
General Information
Reactants and reagents were purchased from commercial suppliers.
All solvents were dried and freshly distilled. TLC was performed on
silica HSGF254 plates. Melting points were determined with a
digital melting-point apparatus. 1H and 13C NMR spectra were
obtained from a solution in deuterated chloroform (CDCl3) with
tetramethylsilane as an internal standard using a 400/101 MHz
(1H/13C) spectrometer. Chemical shifts (δ) are given in ppm and
coupling constants (J) in Hz. Multiplicities are reported as follows:
singlet (s), doublet (d), doublet of doublets (dd), triplet (t), quartet
(q), and multiplet (m). Column chromatography was performed on
silica gel 300–400 mesh. The structures of known compounds were
further corroborated by comparing their 1H, 13C NMR data with
those of literature. High-resolution mass spectra (HRMS) analyses
were carried out on an electron impact ion source (EI) apparatus
using time-of-flflight (TOF) mass spectrometry.
[a] Reaction conditions: 2-naphthoic acid (0.5 mmol), disulfide (0.6 mmol),
Ni(dppp)Cl2 (10 mol%), dppp (40 mol%), Piv2O (1.5 equiv.), Mn (1 mmol),
°
Zn (0.75 mmol) and toluene (2 mL), 160 C, 24 h. [b] Isolated yields.
[c] dppp (20 mol%).
General procedure for synthesis of substrates. K2CO3 (0.25 mmol,
34.5 mg) was added to a 25 mL tube with a magnetic bar. MeCN
(10 mL) and aryl thiols (20 mmol) were added and then the mixture
°
was stirred at 30 C under air and monitored by TLC. The solution
was diluted with ethyl acetate (10 mL), and evaporated under
vacuum. The crude reaction mixture was purified by column
chromatograhy on silica gel (petroleum ether/ethyl acetate) to
afford product 2.[20]
Scheme 3. Mechanistic experiments
General Procedure for the Synthesis of Aryl Sulfide (3a–3l and
4a–4ae). Carboxylic acid (0.5 mol), disulfide (0.6 mmol), Ni(dppp)Cl2
(0.05 mmol, 27 mg), dppp (0.2 mmol, 83 mg), Piv2O (0.75 mmol,
140 mg), Mn (1 mmol, 55 mg) and Zn (0.75 mmol, 49 mg) were
successively added into a 15 mL sealed tube, using anhydrous
°
toluene (2 mL) as the solvent. The mixture was stirred in a 160 C oil
bath under nitrogen for 24 h. Upon completion of the reaction as
indicated by TLC, the mixture was diluted with EtOAc and then
filtered through a pad of celite. The solvent was removed under
vacuum. The residue was purified on a silica column (petroleum
ether/ethyl acetate) to give the pure target product.
General Procedure for the Synthesis of Aryl Selenide (5a–5h).
Carboxylic acid (0.5 mol), diselenide (0.6 mmol), Ni(dppp)Cl2
(0.05 mmol, 27 mg), dppp (0.2 mmol, 83 mg), Piv2O (0.75 mmol,
140 mg), Mn (1 mmol, 55 mg) and Zn (0.75 mmol, 49 mg) were
successively added into a 15 mL sealed tube, using anhydrous
Scheme 4. Proposed reaction mechanism.
added with Ni(0) to obtain acyl nickel (II) intermediate E.
Intermediate E has undergone decarbonylation and reductive
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Table 3. Substrate scope of carboxylic acids.[a,b]
[a] Reaction conditions: carboxylic acid (0.5 mmol), 1,2-bis(4-methoxyphenyl)disulfane (0.6 mmol), Ni(dppp)Cl2 (10 mol%), dppp (40 mol%), Piv2O (1.5 equiv.),
°
Mn (1 mmol), Zn (0.75 mmol) and toluene (2 mL), 160 C, 24 h. [b] Isolated yields.
Table 4. Substrate scope of diselenides.[a,b]
°
toluene (2 mL) as the solvent. The mixture was stirred in a 150 C oil
bath under nitrogen for 24 h. Upon completion of the reaction as
indicated by TLC, the mixture was diluted with EtOAc and then
filtered through a pad of celite. The solvent was removed under
vacuum. The residue was purified on a silica column (petroleum
ether/ethyl acetate) to give the pure target product.
1,2-di-o-tolyldisulfane (2a)[21] 1H NMR (400 MHz, CDCl3) δ 7.55–7.46
(m, 2H), 7.18–7.07 (m, 6H), 2.41 (s, 6H).
1,2-bis(2-methoxyphenyl)disulfane (2b)[20] 1H NMR (400 MHz,
CDCl3) δ 7.52 (d, J=7.6 Hz, 2H), 7.18 (t, J=7.6 Hz, 2H), 6.90 (t, J=
7.4 Hz, 2H), 6.85 (d, J=8.0 Hz, 2H), 3.89 (s, 6H).
1,2-bis(3-fluorophenyl)disulfane (2c)[21] 1H NMR (400 MHz, CDCl3) δ
7.31–7.24 (m, 4H), 7.22 (dd, J=7.0, 1.9 Hz, 2H), 6.96–6.89 (m, 2H).
1,2-Bis(4-fluorophenyl)disulfane (2d)[20] 1H NMR (400 MHz, CDCl3) δ
7.43 (dd, J=8.2, 5.3 Hz, 4H), 6.99 (t, J=8.5 Hz, 4H).
1,2-Bis(4-(trifluoromethyl)phenyl)disulfane (2e)[20] 1H NMR
(400 MHz, CDCl3) δ 7.61–7.54 (m, 8H).
[a] Reaction conditions: carboxylic acid (0.5 mmol), diselenide (0.6 mmol),
Ni(dppp)Cl2 (10 mol%), dppp (40 mol%), Piv2O (1.5 equiv.), Mn (1 mmol),
°
Zn (0.75 mmol) and toluene (2 mL), 150 C, 24 h. [b] Isolated yields.
1,2-Bis(4-(tert-butyl)phenyl)disulfane (2f)[21] 1H NMR (400 MHz,
CDCl3) δ 7.44 (d, J=8.2 Hz, 4H), 7.32 (d, J=8.3 Hz, 4H), 1.29 (s, 18H).
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1,2-Bis(4-methoxyphenyl)disulfane (2g)[20] 1H NMR (400 MHz,
CDCl3) δ 7.39 (d, J=8.4 Hz, 4H), 6.82 (d, J=8.4 Hz, 4H), 3.77 (s, 6H).
{1H} NMR (101 MHz, CDCl3) δ 137.6 (s), 134.3 (s), 133.7 (s), 132.1 (s),
132.0 (s), 131.4 (s), 130.1 (s), 128.7 (s), 128.4 (s), 127.9 (s), 127.7 (s),
127.3 (s), 126.5 (s), 125.9 (s), 21.1 (s).
(4-Chlorophenyl)(naphthalen-2-yl)sulfane (3a)[22] The title com-
pound was isolated by column chromatography (petroleum ether)
Naphthalen-2-yl(o–tolyl)sulfane (3h)[11] The title compound was
isolated by column chromatography (petroleum ether) as a color-
less oil (115 mg, 92% yield). 1H NMR (400 MHz, CDCl3) δ 7.77 (d, J=
7.5 Hz, 1H), 7.73 (d, J=8.6 Hz, 1H), 7.70–7.61 (m, 2H), 7.48–7.39 (m,
2H), 7.36–7.27 (m, 2H), 7.27–7.19 (m, 2H), 7.15 (t, J=7.3 Hz, 1H),
2.40 (s, 3H).13C{1H} NMR (101 MHz, CDCl3) δ 139.9 (s), 133.8 (d, J=
9.2 Hz), 133.5 (s), 132.9 (s), 131.9 (s), 130.6 (s), 128.7 (s), 128.1 (s),
127.9 (s), 127.69 (s), 127.66 (s), 127.2 (s), 126.7 (s), 126.5 (s), 125.8 (s),
20.6 (s).
1
°
as a white solid (108 mg, 80% yield). mp 101.5–103.0 C. H NMR
(400 MHz, CDCl3) δ 7.84 (s, 1H), 7.83–7.71 (m, 3H), 7.52–7.45 (m, 2H),
7.38 (d, J=8.5 Hz, 1H), 7.30–7.25 (m, 4H). 13C{1H} NMR (101 MHz,
CDCl3) δ 134.7 (s), 133.7 (s), 133.0 (s), 132.4 (s), 132.3 (s), 131.9 (s),
130.3 (s), 129.3 (s), 129.1 (s), 128.7 (s), 127.7 (s), 127.4 (s), 126.7 (s),
126.4 (s).
(4-Fluorophenyl)(naphthalen-2-yl)sulfane (3b)[22] The title com-
pound was isolated by column chromatography (petroleum ether)
1
as a white solid (102 mg, 80% yield). mp 70.2–71.7 C. H NMR
(4-(Tert-butyl)phenyl)(naphthalen-2-yl)sulfane (3i)[22] The title
compound was isolated by column chromatography (petroleum
ether) as a colorless oil (111 mg, 76% yield). 1H NMR (400 MHz,
CDCl3) δ 7.81–7.66 (m, 4H), 7.49–7.40 (m, 2H), 7.38 (d, J=8.6 Hz,
1H), 7.33 (s, 4H), 1.31 (s, 9H). 13C{1H} NMR (101 MHz, CDCl3) δ 150.5
(s), 133.8 (s), 133.8 (s), 132.1 (s), 131.7 (s), 131.3 (s), 128.9 (s), 128.7
(s), 128.3 (s), 127.7 (s), 127.3 (s), 126.4 (s), 126.0 (s), 34.5 (s), 31.2 (s).
°
(400 MHz, CDCl3) δ 7.78 (d, J=8.0 Hz, 1H), 7.77–7.67 (m, 3H), 7.51–
7.43 (m, 2H), 7.43–7.37 (m, 2H), 7.34 (d, J=8.5 Hz, 1H), 7.03 (t, J=
8.5 Hz, 2H). 13C{1H} NMR (101 MHz, CDCl3) δ 162.4 (d, JC-F =246 Hz),
134.0 (s), 133.9 (s), 133.8 (s), 133.7 (s), 132.1 (s), 130.3 (d, JC-F
=
3.4 Hz), 128.9 (s), 128.6 (s), 127.8 (d, JC-F =10.6 Hz), 127.3 (s), 126.7
(s), 126.1 (s), 116.4 (d, JC-F =21.9 Hz).
Naphthalen-2-yl(4-(trifluoromethyl)phenyl)sulfane (3c)[23] The title
Naphthalen-2-yl(phenyl)sulfane (3j)[22] The title compound was
compound was isolated by column chromatography (petroleum
isolated by column chromatography (petroleum ether) as a white
1
ether) as a white solid (118 mg, 78% yield). mp 105.4–107.1 C. H
solid (104 mg, 88% yield). mp 55.4–57.1 C. 1H NMR (400 MHz,
°
°
NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 7.89–7.83 (m, 2H), 7.83–7.77
(m, 1H), 7.59–7.51 (m, 2H), 7.51–7.43 (m, 3H), 7.30 (d, J=8.1 Hz, 2H).
13C{1H} NMR (101 MHz, CDCl3) δ 142.8 (d, J=1.2 Hz), 133.8 (s), 133.0
(s), 132.9 (s), 130.2 (s), 129.6 (s), 129.4 (s), 128.3 (s), 127.8 (s), 127.7
CDCl3) δ 7.84 (s, 1H), 7.82–7.70 (m, 3H), 7.53–7.43 (m, 2H), 7.43–7.35
(m, 3H), 7.35–7.26 (m, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 135.8 (s),
133.8 (s), 133.0 (s), 132.3 (s), 130.9 (s), 129.9 (s), 129.2 (s), 128.8 (s),
128.7 (s), 127.7 (s), 127.4 (s), 127.0 (s), 126.6 (s), 126.2 (s).
(s), 127.0 (s), 126.9 (s), 125.8 (q, JC-F =3.7 Hz), 122.7 (q, JC-F
272.9 Hz).
=
Cyclohexyl(naphthalen-2-yl)sulfane (3k)[24] The title compound
was isolated by column chromatography (petroleum ether) as a
1
(3-Fluorophenyl)(naphthalen-2-yl)sulfane (3d) The title compound
colorless oil (75 mg, 62% yield). H NMR (400 MHz, CDCl3) δ 7.85 (s,
was isolated by column chromatography (petroleum ether) as a
1H), 7.82–7.69 (m, 3H), 7.53–7.38 (m, 3H), 3.29–3.16 (m, 1H), 2.02 (d,
J=12.5 Hz, 2H), 1.85–1.72 (m, 2H), 1.68–1.58 (m, 1H), 1.48–1.27 (m,
5H). 13C{1H} NMR (101 MHz, CDCl3) δ 133.6 (s), 132.6 (s), 132.0 (s),
130.1 (s), 129.6 (s), 128.2 (s), 127.6 (s), 127.2 (s), 126.4 (s), 125.8 (s),
46.5 (s), 33.34 (s), 26.0 (s), 25.8 (s).
1
°
white solid (100 mg, 79% yield). mp 60.5–61.5 C. H NMR (400 MHz,
CDCl3) δ 7.94 (s, 1H), 7.87–7.75 (m, 3H), 7.54–7.48 (m, 2H), 7.44 (dd,
J=8.6, 1.7 Hz, 1H), 7.22 (dd, J=8.1, 6.1 Hz, 1H), 7.07 (dd, J=7.8,
0.7 Hz, 1H), 6.97 (dt, J=9.3, 1.8 Hz, 1H), 6.89 (td, J=8.4, 2.5 Hz, 1H).
13C{1H} NMR (101 MHz, CDCl3) δ 163.0 (d, JC-F =249.4 Hz), 139.2 (d,
Methyl 3-(naphthalen-2-ylthio)propanoate (3l) The title com-
pound was isolated by column chromatography (eluent: EtOAc/
petroleum ether=1/40) as a colorless oil (66 mg, 54% yield). 1H
NMR (400 MHz, CDCl3) δ 7.83–7.71 (m, 4H), 7.53–7.41 (m, 3H), 3.68
(s, 3H), 3.27 (t, J=7.3 Hz, 2H), 2.68 (t, J=7.3 Hz, 2H). 13C{1H} NMR
(101 MHz, CDCl3) δ 172.2 (s), 133.7 (s), 132.6 (s), 132.0 (s), 128.6 (s),
128.1 (s), 127.8 (s), 127.7 (s), 127.2 (s), 126.6 (s), 125.9 (s), 51.8 (s),
34.2 (s), 28.9 (s). HRMS (EI) m/z calcd for C14H14O2S [M]+: 246.0715,
found: 246.0721
J
C-F =7.7 Hz), 133.8 (s), 132.7 (s), 131.8 (s), 131.0 (s), 130.3 (d, JC-F
=
=
=
8.5 Hz), 129.6 (s), 129.2 (s), 127.7 (d, JC-F =17.9 Hz), 126.7 (d, JC-F
6.2 Hz), 125.1 (d, JC-F =3.0 Hz), 116.4 (d, JC-F =23.4 Hz), 113.5 (d, JC-F
21.4 Hz). HRMS (EI) m/z calcd for C16H11FS [M]+: 254.0566, found:
254.0566
(2-methoxyphenyl)(naphthalen-2-yl)sulfane (3e)[11] The title com-
pound was isolated by column chromatography (eluent: EtOAc/
petroleum ether=1/300) as a colorless oil (102 mg, 77% yield). H
NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 7.82–7.68 (m, 3H), 7.52–7.43
(m, 2H), 7.41 (d, J=8.6 Hz, 1H), 7.26 (d, J=8.1 Hz, 1H), 7.11 (d, J=
7.4 Hz, 1H), 6.92 (d, J=8.1 Hz, 1H), 6.86 (t, J=7.3 Hz, 1H), 3.87 (s,
3H). 13C{1H} NMR (101 MHz, CDCl3) δ 157.32 (s), 133.83 (s), 132.3 (s),
131.9 (s), 131.7 (s), 130.2 (s), 129.0 (s), 128.7 (s), 128.4 (s), 127.7 (s),
127.4 (s), 126.4 (s), 126.1 (s), 124.0 (s), 121.3 (s), 110.9 (s), 55.9 (s).
1
(4-Methoxyphenyl)(phenyl)sulfane (4a)[25] The title compound was
isolated by column chromatography (petroleum ether) as a color-
1
less oil (89 mg, 82% yield). H NMR (400 MHz, CDCl3) δ 7.41 (d, J=
8.5 Hz, 2H), 7.25–7.19 (m, 2H), 7.19–7.10 (m, 3H), 6.89 (d, J=8.6 Hz,
2H), 3.81 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.8 (s), 138.6 (s),
135.3 (s), 128.9 (s), 128.2 (s), 125.7 (s), 124.3 (s), 115.0 (s), 55.3 (s).
(4-methoxyphenyl)(naphthalen-2-yl)sulfane (3f)[22] The title com-
pound was isolated by column chromatography (eluent: EtOAc/
petroleum ether=1/300) as a white solid (117 mg, 88% yield). mp
67.7–69.0 C. H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H), 7.73–7.64 (m,
2H), 7.59 (s, 1H), 7.49–7.38 (m, 4H), 7.29 (d, J=8.4 Hz, 1H), 6.91 (d,
J=8.6 Hz, 2H), 3.83 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.8 (s),
135.9 (s), 135.2 (s), 133.7 (s), 131.7 (s), 128.5 (s), 127.7 (s), 127.1 (s),
126.7 (s), 126.5 (s), 126.4 (s), 125.6 (s), 124.4 (s), 115.0 (s), 55.5 (s).
(4-Methoxyphenyl)(p-tolyl)sulfane (4b)[25] The title compound was
isolated by column chromatography (petroleum ether) as a color-
1
less oil (92 mg, 80% yield). H NMR (400 MHz,CDCl3) δ 7.36 (d, J=
1
°
8.5 Hz, 2H), 7.13 (d, J=8.0 Hz, 2H), 7.06 (d, J=7.9 Hz, 2H), 6.86 (d,
J=8.5 Hz, 2H), 3.80 (s, 3H), 2.30 (s, 3H). 13C{1H} NMR (101 MHz,
CDCl3) δ 159.4 (s), 136.1 (s), 134.3 (s), 134.3 (s), 129.7 (s), 129.3 (s),
125.6 (s), 114.8 (s), 55.3 (s), 21.0 (s).
(4-Methoxyphenyl)(m-tolyl)sulfane (4c)[26] The title compound was
Naphthalen-2-yl(p–tolyl)sulfane (3g)[22] The title compound was
isolated by column chromatography (petroleum ether) as a color-
isolated by column chromatography (petroleum ether) as a white
1
less oil (114 mg, 99% yield). H NMR (400 MHz, CDCl3) δ 7.43–7.40
solid (104 mg, 83% yield). mp 68.7–70.1 C. 1H NMR (400 MHz,
°
(m, 1H), 7.40–7.37 (m, 1H), 7.15–7.09 (m, 1H), 7.01 (s, 1H), 6.98–6.93
(m, 2H), 6.91–6.89 (m, 1H), 6.88–6.85 (m, 1H), 3.81 (s, 3H), 2.27 (s,
3H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.7 (s), 138.7 (s), 138.1 (s),
CDCl3) δ 7.77 (d, J=7.5 Hz, 1H), 7.75–7.66 (m, 3H), 7.49–7.40 (m,
2H), 7.34 (t, J=8.6 Hz, 3H), 7.14 (d, J=7.7 Hz, 2H), 2.35 (s, 3H). 13C
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135.1 (s), 128.9 (s), 128.8 (s), 126.7 (s), 125.5 (s), 124.6 (s), 114.9 (s),
55.3 (s), 21.3 (s).
135.8 (s), 132.1 (q, JC-F =234.9 Hz), 129.0 (s), 123.4 (s), 121.6 (s),119.1
(s) 115.2 (s), 55.4 (s).
(3,5-Dimethylphenyl)(4-methoxyphenyl)sulfane (4d)[25] The title
compound was isolated by column chromatography (petroleum
ether) as a colorless oil (93 mg, 76% yield). 1H NMR (400 MHz,
CDCl3) δ 7.39 (d, J=8.0 Hz, 2H), 6.88 (d, J=8.0 Hz, 2H), 6.79 (d, J=
13.3 Hz, 3H), 3.81 (s, 3H), 2.22 (s, 6H). 13C{1H} NMR (101 MHz, CDCl3)
δ 159.6 (s), 138.6 (s), 137.7 (s), 135.0 (s), 127.8 (s), 126.2 (s), 124.8 (s),
114.8 (s), 55.3 (s), 21.2 (s).
(4-Chlorophenyl)(4-methoxyphenyl)sulfane (4l)[27] The title com-
pound was isolated by column chromatography (petroleum ether)
as a white solid (75 mg, 60% yield). mp 64.7–65.6 C. 1H NMR
°
(400 MHz, CDCl3) δ 7.40 (d, J=8.2 Hz, 2H), 7.19 (d, J=8.1 Hz, 2H),
7.07 (d, J=8.1 Hz, 2H), 6.90 (d, J=8.2 Hz, 2H), 3.83 (s, 3H). 13C{1H}
NMR (101 MHz, CDCl3) δ 160.0 (s), 137.3 (s), 135.5 (s), 131.6 (s), 129.3
(s), 129.0 (s), 123.7 (s), 115.1 (s), 55.4 (s).
(4-Methoxyphenyl)(o–tolyl)sulfane (4e)[26] The title compound was
(3-Chlorophenyl)(4-methoxyphenyl)sulfane (4m)[28] The title com-
isolated by column chromatography (petroleum ether) as a color-
pound was isolated by column chromatography (petroleum ether)
1
1
less oil (70 mg, 61% yield). H NMR (400 MHz, CDCl3) δ 7.33 (d, J=
as a colorless oil (77 mg, 62% yield). H NMR (400 MHz, CDCl3) δ
8.3 Hz, 2H), 7.17 (d, J=6.9 Hz, 1H), 7.12–7.02 (m, 2H), 6.97 (d, J=
7.2 Hz, 1H), 6.89 (d, J=8.3 Hz, 2H), 3.81 (s, 3H), 2.38 (s, 3H). 13C{1H}
NMR (101 MHz, CDCl3) δ 159.5 (s), 137.03 (s), 136.99 (s), 134.5 (s),
130.2 (s), 129.0 (s), 126.4 (s), 126.1 (s), 124.4 (s), 115.0 (s), 55.3 (s),
20.3 (s).
7.44 (d, J=8.3 Hz, 2H), 7.14 (t, J=7.7 Hz, 1H), 7.07 (d, J=9.3 Hz, 2H),
7.00 (d, J=7.5 Hz, 1H), 6.93 (d, J=8.3 Hz, 2H), 3.84 (s, 3H). 13C{1H}
NMR (101 MHz, CDCl3) δ 160.3 (s), 141.3 (s), 136.1 (s), 134.8 (s), 129.8
(s), 127.0 (s), 125.6 (s), 125.4 (s), 122.6 (s), 115.2 (s), 55.4 (s).
(4-Fluorophenyl)(4-methoxyphenyl)sulfane (4n)[27] The title com-
(4-Methoxyphenyl)(naphthalen-1-yl)sulfane (4f)[27] The title com-
pound was isolated by column chromatography (petroleum ether)
1
pound was isolated by column chromatography (petroleum ether)
as a colorless oil (86 mg, 74% yield). H NMR (400 MHz, CDCl3) δ
as a white solid (88 mg, 66% yield). mp 105.3-106.5 C. 1H NMR
7.36 (d, J=8.4 Hz, 2H), 7.23–7.13 (m, 2H), 6.95 (t, J=8.5 Hz, 2H), 6.88
(d, J=8.4 Hz, 2H), 3.81 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 162.8
(d, JC-F =246.8 Hz), 159.6 (s), 134.5 (s), 133.1 (d, JC-F =3.3 Hz), 131.0
(d, JC-F =8.0 Hz), 125.2 (s), 116.2 (d, JC-F =22.0 Hz), 115.0 (s), 55.4 (s).
°
(400 MHz, CDCl3) δ 8.37 (d, J=7.6 Hz, 1H), 7.84 (d, J=7.4 Hz, 1H),
7.72 (d, J=6.6 Hz, 1H), 7.57–7.45 (m, 2H), 7.33 (d, J=7.0 Hz, 4H),
6.86 (d, J=8.2 Hz, 2H), 3.78 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ
159.3 (s), 134.6 (s), 133.9 (s), 133.8 (s), 132.2 (s), 128.5 (s), 128.4 (s),
127.4 (s), 126.5 (s), 126.3 (s), 125.7 (s), 125.1 (s), 124.9 (s), 114.98 (s).
(3,5-Difluorophenyl)(4-methoxyphenyl)sulfane (4o)[30] The title
compound was isolated by column chromatography (petroleum
ether) as a colorless oil (103 mg, 82% yield). 1H NMR (400 MHz,
CDCl3) δ 7.46 (d, J=8.2 Hz, 2H), 6.95 (d, J=8.2 Hz, 2H), 6.60–6.47
(4-(Tert-butyl)phenyl)(4-methoxyphenyl)sulfane (4g)[27] The title
compound was isolated by column chromatography (petroleum
ether) as a colorless oil (117 mg, 86% yield). 1H NMR (400 MHz,
CDCl3) δ 7.39 (d, J=7.9 Hz, 2H), 7.28–7.23 (m, 2H), 7.13 (d, J=
7.6 Hz, 2H), 6.88 (d, J=7.8 Hz, 2H), 3.80 (s, 3H), 1.28 (s, 9H). 13C{1H}
NMR (101 MHz, CDCl3) δ 159.6 (s), 149.2 (s), 134.8 (s), 134.6 (s), 128.5
(s), 126.0 (s), 125.1 (s), 114.9 (s), 55.3 (s), 34.4 (s), 31.3 (s).
(m, 3H), 3.85 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 164.3 (d, JC-F
=
13.2 Hz), 161.8 (d, JC-F =13.2 Hz), 160.8 (s), 144.0 (t, JC-F =9.6 Hz),
136.9 (s), 132.0 (s), 121.1 (s), 115.4 (s), 114.9 (s), 109.2 (d, JC-F
=
7.6 Hz), 109.0 (d, JC-F =7.6 Hz), 100.6 (t, JC-F =25.8 Hz), 55.4 (s).
(4-Methoxyphenyl)(3-(trifluoromethyl)phenyl)sulfane (4p)[25] The
title compound was isolated by column chromatography (petro-
leum ether) as a colorless oil (100 mg, 70% yield). 1H NMR
(400 MHz, CDCl3) δ 7.45 (d, J=8.3 Hz, 2H), 7.39–7.28 (m, 3H), 7.24
(d, J=8.8 Hz, 1H), 6.94 (d, J=8.3 Hz, 2H), 3.84 (s, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 160.4 (s), 140.8 (s), 136.2 (s), 131.6 (d, JC-F=
32.5 Hz), 130.9 (d, JC-F =32.4 Hz), 130.3 (d, JC-F =1.1 Hz), 129.2 (s),
123.8 (q, JC-F =3.9 Hz), 122.4 (s), 122.3 (s), 122.1 (q, JC-F =3.8 Hz),
115.3 (s), 55.4 (s).
(4-Isopropylphenyl)(4-methoxyphenyl)sulfane (4h)[28] The title
compound was isolated by column chromatography (petroleum
ether) as a colorless oil (84 mg, 65% yield). 1H NMR (400 MHz,
CDCl3) δ 7.38 (d, J=8.6 Hz, 2H), 7.20–7.03 (m, 4H), 6.87 (d, J=
8.6 Hz, 2H), 3.80 (s, 3H), 2.91–2.79 (m, 1H), 1.21 (d, J=6.9 Hz, 6H).
13C{1H} NMR (101 MHz, CDCl3) δ 159.5 (s), 147.0 (s), 134.8 (s), 134.6
(s), 129.0 (s), 127.1 (s), 125.3 (s), 114.8 (s), 55.3 (s), 33.6 (s), 23.9 (s).
(3,5-Dimethoxyphenyl)(4-methoxyphenyl)sulfane (4i) The title
compound was isolated by column chromatography (eluent:
EtOAc/petroleum ether=1/40) as a yellow oil (127 mg, 92% yield).
1H NMR (400 MHz, CDCl3) δ 7.44 (d, J=8.3 Hz, 2H), 6.90 (d, J=
8.3 Hz, 2H), 6.28 (s, 2H), 6.23 (s, 1H), 3.82 (s, 3H), 3.71 (s, 6H). 13C{1H}
NMR (101 MHz, CDCl3) δ 160.9 (s), 160.0 (s), 141.0 (s), 135.9 (s), 123.3
(s), 115.0 (s), 105.6 (s), 97.9 (s), 55.31 (s), 55.27 (s). HRMS (EI) m/z
calcd for C15H16O3S [M]+ : 276.0820, found: 276.0824
(4-Methoxyphenyl)(4-(trifluoromethyl)phenyl)sulfane (4q)[11] The
title compound was isolated by column chromatography (petro-
°
leum ether) as a white solid (101 mg, 71% yield). mp 83.5-85.1 C.
1H NMR (400 MHz, CDCl3) δ 7.45 (dd, J=13.6, 8.1 Hz, 4H), 7.13 (d,
J=7.9 Hz, 2H), 6.95 (d, J=7.8 Hz, 2H), 3.85 (s, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 160.6 (s), 144.8 (s), 136.7 (s), 126.4 (s), 125.6 (q,
J
C-F =3.8 Hz), 122.8 (q, JC-F =272.7 Hz), 121.6 (s), 115.4 (s), 55.4 (s).
(4-Methoxyphenyl)(3,4,5-trimethoxyphenyl)sulfane (4j)[29] The ti-
tle compound was isolated by column chromatography (eluent:
4-((4-Methoxyphenyl)thio)benzonitrile (4r)[27] The title compound
was isolated by column chromatography (eluent: EtOAc/petroleum
EtOAc/petroleum ether=1/20) as a white solid (103 mg, 67% yield).
ether=1/30) as a white solid (115 mg, 95% yield). mp 102.5-
1
1
°
°
mp 122.2–123.5 C. H NMR (400 MHz, CDCl3) δ 7.39 (d, J=8.3 Hz,
103.6 C. H NMR (400 MHz, CDCl3) δ 7.46 (t, J=9.3 Hz, 4H), 7.07 (d,
2H), 6.89 (d, J=8.3 Hz, 2H), 6.47 (s, 2H), 3.82 (d, J=2.8 Hz, 6H), 3.76
(s, 6H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.6 (s), 153.5 (s), 136.7 (s),
134.4 (s), 132.7 (s), 125.1(s), 114.9 (s), 106.5 (s), 60.9 (s), 56.1 (s), 55.4
(s).
J=8.3 Hz, 2H), 6.97 (d, J=8.5 Hz, 2H), 3.86 (s, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 160.9 (s), 147.3 (s), 137.1 (s), 132.2 (s), 126.0 (s),
120.3 (s), 118.9 (s), 115.5 (s), 108.0 (s), 55.4 (s).
1-(4-((4-Methoxyphenyl)thio)phenyl)ethan-1-one (4s)[26] The title
compound was isolated by column chromatography (eluent:
EtOAc/petroleum ether=1/30) as a yellow oil (93 mg, 72% yield).
1H NMR (400 MHz, CDCl3) δ 7.78 (d, J=8.0 Hz, 2H), 7.48 (d, J=
8.0 Hz, 2H), 7.09 (d, J=8.0 Hz, 2H), 6.96 (d, J=8.0 Hz, 2H), 3.85 (s,
3H), 2.53 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 197.1 (s), 160.6 (s),
146.9 (s), 136.8 (s), 133.8 (s), 128.8 (s), 125.8 (s), 121.3 (s), 115.3 (s),
55.4 (s), 26.4 (s).
(4-Methoxyphenyl)(4-(trifluoromethoxy)phenyl)sulfane
(4k)[27]
The title compound was isolated by column chromatography
(petroleum ether) as a colorless oil (126 mg, 84% yield). 1H NMR
(400 MHz, CDCl3) δ 7.42 (d, J=8.2 Hz, 2H), 7.14 (d, J=8.4 Hz, 2H),
7.07 (d, J=8.2 Hz, 2H), 6.91 (d, J=8.2 Hz, 2H), 3.81 (s, 3H). 13C{1H}
NMR (101 MHz, CDCl3) δ 160.2 (s), 147.2 (d, JC-F =1.6 Hz), 137.8 (s),
Eur. J. Org. Chem. 2021, 2452–2461
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Methyl 4-((4-methoxyphenyl)thio)benzoate (4t)[31] The title com-
pound was isolated by column chromatography (eluent: EtOAc/
111.2 (s), 55.3 (s). HRMS (EI) m/z calcd for C15H12O2S [M]+ : 256.0558,
found: 256.0557
petroleum ether=1/30) as a yellow solid (120 mg, 88% yield). mp
2-((4-Methoxyphenyl)thio)thiophene (4ab)[35] The title compound
was isolated by column chromatography (petroleum ether) as a
colorless oil (50 mg, 45% yield). 1H NMR (400 MHz, CDCl3) δ 7.37 (d,
J=5.1 Hz, 1H), 7.28 (d, J=8.6 Hz, 2H), 7.20 (d, J=2.6 Hz, 1H), 7.02–
6.96 (m, 1H), 6.82 (d, J=8.6 Hz, 2H), 3.77 (s, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 158.9 (s), 134.3 (s), 133.9 (s), 131.1 (s), 123.0 (s),
128.3 (s), 127.6 (s), 114.7 (s), 55.3 (s).
1
°
92.5-93.3 C. H NMR (400 MHz, CDCl3) δ 7.85 (d, J=8.1 Hz, 2H), 7.47
(d, J=8.3 Hz, 2H), 7.08 (d, J=8.1 Hz, 2H), 6.95 (d, J=8.3 Hz, 2H),
3.87 (s, 3H), 3.85 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 166.8 (s),
160.6 (s), 146.4 (s), 136.7 (s), 129.9 (s), 126.7 (s), 125.8 (s), 121.6 (s),
115.3 (s), 55.4 (s), 52.0 (s).
[1,1’-biphenyl]-4-yl(4-methoxyphenyl)sulfane (4u)[26] The title
compound was isolated by column chromatography (petroleum
2-((4-Methoxyphenyl)thio)furan (4ac) The title compound was
ether) as a white solid (121 mg, 83% yield). mp 96.5–97.8 C. 1H
°
isolated by column chromatography (petroleum ether) as a color-
NMR (400 MHz, CDCl3) δ 7.54 (d, J=7.5 Hz, 2H), 7.48–7.39 (m, 6H),
7.32 (t, J=7.2 Hz, 1H), 7.23 (d, J=8.3 Hz, 2H), 6.92 (d, J=8.5 Hz, 2H),
3.83 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.9 (s), 140.4 (s),
138.7 (s), 137.8 (s), 135.4 (s), 128.8 (s), 128.5 (s), 127.6 (s), 127.2 (s),
126.8 (s), 124.2 (s), 115.0 (s), 55.4 (s).
1
less oil (64 mg, 62% yield). H NMR (400 MHz, CDCl3) δ 7.50 (s, 1H),
7.30–7.24 (m, 2H), 6.81 (d, J=8.6 Hz, 2H), 6.64 (d, J=2.7 Hz, 1H),
6.41 (s, 1H), 3.76 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.0 (s),
145.9 (s), 144.9 (s), 131.1 (s), 125.9 (s), 117.7 (s), 114.7 (s), 111.7 (s),
55.3 (s). HRMS (EI) m/z calcd for C11H10O2S [M]+: 206.0402, found:
206.0405
(E)-(4-Methoxyphenyl)(styryl)sulfane (4v)[32] The title compound
was isolated by column chromatography (petroleum ether) as a
colorless oil (100 mg, 83% yield). 1H NMR (400 MHz, CDCl3) δ 7.40
(d, J=8.5 Hz, 2H), 7.28 (d, J=4.1 Hz, 4H), 7.23–7.15 (m, 1H), 6.90 (d,
J=8.5 Hz, 2H), 6.82 (d, J=15.4 Hz, 1H), 6.50 (d, J=15.4 Hz, 1H), 3.82
(s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.5 (s), 136.7 (s), 133.5 (s),
128.9 (s), 128.6 (s), 127.2 (s), 125.8 (s), 125.7 (s), 124.5 (s), 114.9 (s),
55.4 (s).
6-((4-Methoxyphenyl)thio)quinoline (4ad)[36] The title compound
was isolated by column chromatography (petroleum ether) as a
colorless oil (73 mg, 55% yield). 1H NMR (400 MHz, CDCl3) δ 8.81 (d,
J=1.8 Hz, 1H), 7.96 (d, J=8.4 Hz, 2H), 7.53–7.43 (m, 4H), 7.36–7.29
(m, 1H), 6.95 (d, J=8.2 Hz, 2H), 3.84 (s, 3H). 13C{1H} NMR (101 MHz,
CDCl3) δ 160.2 (s), 149.7 (s), 146.6 (s), 137.8 (s), 135.9 (s), 135.0 (s),
129.8 (s), 129.5 (s), 128.6 (s), 124.8 (s), 123.1 (s), 121.5 (s), 115.2 (s),
55.3 (s).
3-((4-Methoxyphenyl)thio)thiophene (4w)[31] The title compound
was isolated by column chromatography (petroleum ether) as a
colorless oil (80 mg, 72% yield). H NMR (400 MHz, CDCl3) δ 7.35–
7.28 (m, 3H), 7.12 (d, J=1.6 Hz, 1H), 6.94 (d, J=4.6 Hz, 1H), 6.84 (d,
J=8.6 Hz, 2H), 3.79 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 159.1 (s),
132.7 (s), 132.4 (s), 129.7 (s), 126.4 (s), 126.3 (s), 124.3 (s), 114.8 (s),
55.3 (s).
(5-((3r,5r,7r)-Adamantan-1-yl)-6-(4-methoxyphenyl) naphthalen-
2-yl) (phenyl)sulfane (4ae) The title compound was isolated by
column chromatography (eluent: EtOAc/petroleum ether=1/120)
1
as a white solid (193 mg, 76% yield). mp 157.8-158.7 C. 1H NMR
°
(400 MHz, CDCl3) δ 7.94 (s, 1H), 7.86 (s, 1H), 7.82–7.75 (m, 2H), 7.73
(d, J=8.2 Hz, 1H), 7.57 (s, 1H), 7.51 (d, J=8.1 Hz, 1H), 7.42 (d, J=
8.4 Hz, 1H), 7.37 (d, J=6.9 Hz, 2H), 7.31 (t, J=6.6 Hz, 2H), 7.26–7.24
(m, 1H), 6.98 (d, J=8.1 Hz, 1H), 3.89 (s, 3H), 2.18 (s, 6H), 2.10 (s, 3H),
1.80 (s, 6H). 13C{1H} NMR (101 MHz, CDCl3) δ 158.7 (s), 139.4 (s),
138.9 (s), 136.2 (s), 132.9 (s), 132.7 (s), 132.6 (s), 132.3 (s), 130.7 (s),
130.0 (s), 129.3 (s), 129.2 (s), 129.0 (s), 127.8 (s), 126.9 (s), 126.4 (s),
125.9 (s), 125.6 (s), 124.8 (s), 112.1 (s), 55.2 (s), 40.6 (s), 37.2 (s), 37.1
(s), 29.1 (s). HRMS (EI) m/z calcd for C33H32OS [M]+: 476.2174, found:
476.2186
3-((4-Methoxyphenyl)thio)furan (4x)[33] The title compound was
isolated by column chromatography (petroleum ether) as a color-
1
less oil (28 mg, 27% yield). H NMR (400 MHz, CDCl3) δ 7.51 (s, 1H),
7.44 (s, 1H), 7.24 (m, 2H), 6.82 (d, J=8.6 Hz, 2H), 6.37 (s, 1H), 3.78 (s,
3H). 13C{1H} NMR (101 MHz, CDCl3) δ 158.7 (s), 144.5 (s), 143.9 (s),
131.0 (s), 126.9 (s), 116.4 (s), 114.7 (s), 113.9 (s), 55.4 (s).
6-((4-Methoxyphenyl)thio)benzo[d]thiazole (4y) The title com-
pound was isolated by column chromatography (eluent: EtOAc/
petroleum ether=1/20) as a yellow solid (86 mg, 63% yield). mp
Naphthalen-2-yl(phenyl)selane (5a)[37] The title compound was
81.5-82.5 C. 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 7.98 (d, J=
isolated by column chromatography (petroleum ether) as a yellow
°
1
°
8.6 Hz, 1H), 7.66 (s, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.35 (d, J=8.5 Hz,
1H), 6.93 (d, J=8.1 Hz, 2H), 3.84 (s, 3H). 13C{1H} NMR (101 MHz,
CDCl3) δ 160.1 (s), 153.4 (s), 151.5 (s), 136.8 (s), 135.6 (s), 134.8 (s),
126.7 (s), 123.9 (s), 123.7 (s), 120.6 (s), 115.2 (s), 55.4 (s). HRMS (EI)
m/z calcd for C14H11NOS2 [M]+ : 273.0282, found: 273.0281
solid (95 mg, 67% yield). mp 51.2–52.6 C. H NMR (400 MHz, CDCl3)
δ 7.99 (s, 1H), 7.84–7.77 (m, 1H), 7.73 (d, J=7.8 Hz, 2H), 7.50–7.43
(m, 4H), 7.31–7.22 (m, 4H). 13C{1H} NMR (101 MHz, CDCl3) δ 134.0 (s),
132.9 (s), 132.0 (s), 131.2 (s), 130.5 (s), 129.4 (s), 128.8 (s), 128.4 (s),
127.8 (s), 127.4 (s), 127.3 (s), 126.5 (s), 126.21 (s).
2-((4-Methoxyphenyl)thio)-1-methyl-1H-indole (4z)[34] The title
compound was isolated by column chromatography (eluent:
(6-Methoxynaphthalen-2-yl)(phenyl)selane (5b) The title com-
pound was isolated by column chromatography (eluent: EtOAc/
EtOAc/petroleum ether=1/60) as a yellow solid (86 mg, 62% yield).
petroleum ether=1/120) as a white solid (116 mg, 74% yield). mp
1
1
°
°
mp 64.5–65.5 C. H NMR (400 MHz, CDCl3) δ 7.61 (d, J=7.9 Hz, 1H),
106.3–107.5 C. H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.68–7.62
7.32–7.25 (m, 2H), 7.12 (t, J=8.1 Hz, 3H), 6.86 (s, 1H), 6.78 (d, J=
8.6 Hz, 2H), 3.75 (s, 3H), 3.68 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ
158.5 (s), 138.5 (s), 129.7 (s), 129.1 (s), 127.2 (s), 126.8 (s), 122.6 (s),
120.7 (s), 119.8 (s), 114.8 (s), 110.5 (s), 109.7 (s), 55.3 (s), 29.9 (s).
(m, 2H), 7.52 (d, J=8.4 Hz, 1H), 7.46–7.39 (m, 2H), 7.26–7.23 (m, 3H),
7.15 (d, J=9.0 Hz, 1H), 7.10 (s, 1H), 3.91 (s, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 158.1 (s), 133.8 (s), 133.0 (s), 132.1 (s), 132.0 (s),
131.8 (s), 129.5 (s), 129.3 (s), 129.0 (s), 127.7 (s), 126.9 (s), 124.8 (s),
119.3 (s), 105.73 (s), 55.3 (s). HRMS (EI) m/z calcd for C17H14OSe [M]+:
314.0210, found: 314.0217
2-((4-Methoxyphenyl)thio)benzofuran (4aa) The title compound
was isolated by column chromatography (petroleum ether) as a
1
colorless oil (105 mg, 82% yield). H NMR (400 MHz, CDCl3) δ 7.49
Naphthalen-1-yl(phenyl)selane (5c)[38] The title compound was
(d, J=7.7 Hz, 1H), 7.41 (d, J=8.3 Hz, 3H), 7.28–7.23 (m, 1H), 7.19 (t,
J=7.4 Hz, 1H), 6.87–6.84 (m, 2H), 6.84–6.81 (m, 1H), 3.77 (s, 3H). 13C
{1H} NMR (101 MHz, CDCl3) δ 159.6 (s), 156.5 (s), 150.1 (s), 132.9 (s),
128.5 (s), 124.7 (s), 123.5 (s), 122.9 (s), 120.6 (s), 114.9 (s), 111.8 (s),
isolated by column chromatography (petroleum ether) as a yellow
oil (120 mg, 85% yield). H NMR (400 MHz, CDCl3) δ 8.38–8.29 (m,
1H), 7.85 (d, J=7.7 Hz, 2H), 7.77 (d, J=6.9 Hz, 1H), 7.56–7.46 (m,
2H), 7.42–7.31 (m, 3H), 7.23–7.15 (m, 3H). 13C{1H} NMR (101 MHz,
CDCl3) δ 134.1 (s), 134.1 (s), 133.8 (s), 131.68 (s), 131.66 (s), 129.4 (s),
1
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129.3 (s), 129.2 (s), 128.6 (s), 127.6 (s), 126.9 (s), 126.8 (s), 126.3 (s),
126.0 (s).
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[1,1’-Biphenyl]-4-yl(4-methoxyphenyl)selane (5d)[39] The title com-
pound was isolated by column chromatography (petroleum ether)
as a yellow solid (68 mg, 40% yield). mp 69.3–70.2 C. 1H NMR
°
(400 MHz, CDCl3) δ 7.56 (d, J=7.5 Hz, 2H), 7.54–7.46 (m, 6H), 7.43 (t,
J=7.4 Hz, 2H), 7.38–7.31 (m, 1H), 7.31–7.26 (m, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 140.4 (s), 140.3 (s), 133.3 (s), 133.1 (s), 131.0 (s),
130.2 (s), 129.4 (s), 128.8 (s), 128.0 (s), 127.5 (s), 127.4 (s), 126.9 (s).
1-(4-(Phenylselanyl)phenyl)ethan-1-one (5e)[38] The title com-
pound was isolated by column chromatography (eluent: EtOAc/
petroleum ether=1/30) as a yellow solid (71 mg, 55% yield). mp
1
°
59.0–60.3 C. H NMR (400 MHz, CDCl3) δ 7.78 (d, J=7.9 Hz, 2H), 7.58
(d, J=6.1 Hz, 2H), 7.44–7.29 (m, 5H), 2.54 (s, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 197.2 (s), 140.2 (s), 135.1 (s), 135.0 (s), 130.2 (s),
129.7 (s), 128.8 (s), 128.5 (s), 128.4 (s), 26.4 (s).
Phenyl(4-(trifluoromethyl)phenyl)selane (5f)[40] The title com-
pound was isolated by column chromatography (petroleum ether)
as a yellow oil (72 mg, 48% yield). 1H NMR (400 MHz, CDCl3) δ 7.58–
7.54 (m, 2H), 7.48–7.39 (m, 4H), 7.39–7.29 (m, 3H). 13C{1H} NMR
(101 MHz, CDCl3) δ 137.8 (s), 134.8 (s), 133.0 (s), 131.0 (s), 129.7 (s),
128.7 (s), 128.5 (s), 125.9 (q, JC-F =3.8 Hz), 122.7 (q, JC-F =273.0 Hz).
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isolated by column chromatography (eluent: EtOAc/petroleum
ether=1/300) as a yellow oil (74 mg, 56% yield). 1H NMR (400 MHz,
CDCl3) δ 7.48 (s, 2H), 7.36–7.08 (m, 4H), 7.08–6.91 (m, 2H), 6.79 (d,
J=7.9 Hz, 1H), 3.74 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 160.0 (s),
133.2 (s), 132.2 (s), 130.7 (s), 130.0 (s), 129.3 (s), 127.4 (s), 124.9 (s),
118.0 (s), 113.1 (s), 55.2 (s).
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1
petroleum ether=1/300) as a colorless oil (83 mg, 60% yield). H
NMR (400 MHz, CDCl3) δ 7.50 (d, J=8.3 Hz, 1H), 7.21 (dd, J=18.5,
9.2 Hz, 5H), 6.85 (s, 1H), 6.69 (d, J=8.2 Hz, 1H), 3.80 (s, 3H), 2.39 (s,
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132.8 (s), 130.2 (s), 129.1 (s), 126.1 (s), 120.6 (s), 116.1 (s), 112.2 (s),
55.2 (s), 23.1 (s). HRMS (EI) m/z calcd for C14H14OSe [M]+: 278.0210,
found: 278.0209
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Acknowledgements
We gratefully acknowledge the financial support by PAPD (A
Project Funded by the Priority Academic Program Development of
Jiangsu Higher Education Institutions).
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Conflict of Interest
The authors declare no conflict of interest.
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Manuscript received: January 30, 2021
Revised manuscript received: April 6, 2021
Accepted manuscript online: April 19, 2021
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