Utilizing 2-phenylpropanal as coupling partner for C-S bond formation via sequential thioarylation and decarbonylation process: A novel strategy for the synthesis of aryl alkyl sulfides

Article abstract of DOI:10.1002/aoc.5211

In this study, first direct access to aryl alkyl sulfides employing 2-phenylpropanal as coupling partner is reported. Diaryl disulfides react with this aldehyde in the presence of morpholine and produce the corresponding sulfide products in high yields. In another part, disulfides are in situ generated in the reaction mixture from aryl halides/CuI/Cyanodithioformate and coupled with 2-phenylpropanal to access aryl alkyl sulfides.

Full text of DOI:10.1002/aoc.5211

Received: 1 June 2019
DOI: 10.1002/aoc.5211
Revised: 24 July 2019
Accepted: 6 August 2019
F U L L P A P E R
Utilizing 2‐phenylpropanal as coupling partner for C‐S bond
formation via sequential thioarylation and decarbonylation
process: A novel strategy for the synthesis of aryl alkyl
sulfides
Elham Shaikhi Shahidzadeh | Najmeh Nowrouzi
| Mohammad Abbasi
Department of Chemistry, Faculty of
In this study, first direct access to aryl alkyl sulfides employing 2‐
phenylpropanal as coupling partner is reported. Diaryl disulfides react with
this aldehyde in the presence of morpholine and produce the corresponding
sulfide products in high yields. In another part, disulfides are in situ generated
in the reaction mixture from aryl halides/CuI/Cyanodithioformate and coupled
with 2‐phenylpropanal to access aryl alkyl sulfides.
Sciences, Persian Gulf University, Bushehr
75169, Iran
Correspondence
Najmeh Nowrouzi, Department of
Chemistry, Faculty of Sciences, Persian
Gulf University. Bushehr 75169, Iran.
Email: nowrouzi@pgu.ac.ir
KEYWORDS
Funding information
Persian Gulf University Research Council
aryl alkyl sulfide, cuI, C‐S bond formation, decarbonylation, thioarylation
1 | INTRODUCTION
sodium
thioacetate,4c
sulfide,[15]
thiocyanate,[16]
ethyl
xanthogenate,[17]
potassium
Potassium
Aryl alkyl sulfides are valuable building blocks due to
their biological, industrial and chemical applications.[1]
Because of the importance of sulfides in various
branches of science, up to now, many synthetic
approaches have been employed in the synthesis of
these compounds,[2] including the reaction of organic
halides with thiols[3] or organo‐disulfides;[4] coupling of
aryl (alkyl)boronic acids with thiols,[5] N‐thioimide
derivative[6] or disulfides;[7] thioetherification of aro-
matic C‐H bonds with thiols[8] or disulfides;[9] the reac-
tion of aryl triflates with thiols[10] and S‐arylation of
thiols using triphenyltin chloride.[11] All of these cou-
pling reactions have been performed in the presence of
transition metals as catalysts. Though efficient, most of
these methods require foul‐smelling and environmen-
tally unfavorable thiols as a coupling partner or generat-
ing them as stoichiometric byproducts. In an attempt, to
overcome the problems created by thiols, three‐
component reactions have been replaced with two par-
tial ones. In the three‐component strategy, the use of
bad‐smelling thiols is avoided and sulfur‐donor reagents
such as thiourea,[12] thiosulfate,[13] carbon disulfide,[14]
triisopropylsilanethiol[18] and S8,[19] for in situ genera-
tion of thiols have been employed. In spite of many
efforts in the synthesis of aryl alkyl sulfides, there are
still some problems in obtaining these products. Forma-
tion of symmetrical sulfide byproducts, poisoning and
deactivation of catalysts by the organosulfur compounds,
the need for bidentate phosphine ligands or additives
and over‐oxidation of sulfides during the reaction are
examples of these problems. Therefore, to achieve more
effective systems, this field of research is still open.
2 | RESULTS AND DISCUSSION
Recently, we developed efficient methods for the synthe-
sis of organosulfurs.[20] In the continued effort to
develop benign protocols for carbon‐sulfur bond forma-
tion, we attempted to access α‐thioaryl carbonyl com-
pounds employing disulfides and carbonyl compounds.
To achieve this, diphenyl disulfide (0.5 mmol) was
added to
a stirring solution of 2‐phenylpropanal
(0.5 mmol) and K2CO3 (1.5 mmol) in DMF (1 mL) and
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https://doi.org/10.1002/aoc.5211

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SHAIKHI SHAHIDZADEH ET AL.
the reaction mixture was heated at 120 °C. In this case,
a product was formed, but most of the aldehyde
remained intact even after 24 hr (Table 1, entry 1). By
increasing the reaction temperature to 130 °C (Table 1,
entry 2), the product efficiency did not increase and no
complete consumption of aldehyde was observed. In
another attempt, for activation of 2‐phenylpropanal,
0.5 mmol morpholine was added (Table 1, entry 3). In
the presence of morpholine, the yield improved and
afforded a product that, unlike the expectation, did not
contain carbonyl group
contained two signals at 22.3 and 48.0 for methyl and
methine carbons and eight signals at 127.1–143.2 ppm
corresponding to the aromatic carbons (Supporting
Information).
With this rather unexpected result in hand, more
experiments were carried out to increase the product's
efficiency at the appropriate reaction time. Considering
the reaction temperature, morpholine was replaced with
tributylamine and pyridine. In both cases, the product
was formed with excellent efficiency. But, regard to the
price of these compounds, morpholine was selected as
base again (Table 1, entries 4, 5). Increasing the amount
of morpholine to 2.0 mmol did not ameliorate the reac-
tion, but lower amounts led to lower yield (Table 1,
entries 6–8). As shown in entry 9 of Table 1, no sulfane
product was detected in the absence of K2CO3. Further
check in the presence of Na2CO3, K3PO4 lowered the
thioetherification yield (Table 1, entries 10, 11). Increas-
ing the amount of K2CO3 to 2.0 mmol did not affect the
reaction appreciably, while reducing the amount of
K2CO3, reduced the yield (Table 1, entry 12, 13).
After careful structural analysis, the unexpected prod-
uct was assigned to be phenyl(1‐phenylethyl)sulfane,
which indicates that in addition to the thioarylation reac-
tion, decarbonylation also happened (Scheme 1)
The 1H NMR spectrum of isolated compound consisted
of one doublet peak at 1.67 ppm which correlated to the
resonance of CH3 protons. The quartet peak at 4.38 ppm
is related to methine proton. 10 aromatic hydrogen atoms
were appeared as four distinct multiplet signals at 7.21–
7.35 ppm in a 2:2:2:4 ratio. The 13C NMR spectrum
TABLE 1 Effect of different reaction parameters on the synthesis of aryl alkyl sulfides
o
Entry
Base
Additive (mmol)
Solvent
T C
Time (h)
Yield (%)a
1
‐
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
‐
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
H2O
120
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
25
38
2
‐
130
120
3
morpholine (0.5)
tributylamine (0.5)
pyridine (0.5)
80
4
120
83
5
120
78
6
morpholine (1.0)
morpholine (2.0)
morpholine (0.4)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
morpholine (0.5)
120
83
7
120
83
8
120
69
9
120
‐
10
11
12
13
14
15
16
17
18
19
Na2CO3 (1.5)
K3PO4 (1.5)
K2CO3 (2.0)
K2CO3 (1.0)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
K2CO3 (1.5)
120
60
120
56
120
80
120
55
100
‐
MeCN
toluene
PEG‐200
DMF
DMF
reflux
reflux
120
trace
62
trace
91
130
100
50
aIsolated yield.

SHAIKHI SHAHIDZADEH ET AL.
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SCHEME 1 Unexpected formation of
aryl alkyl sulfide
Screening of solvents revealed that DMF was the most
effective solvent in this coupling reaction and other sol-
vents such as H2O, MeCN, toluene and PEG‐200 were
less effective (Table 1, entries 14–17). Finally,
thioetherification reaction carried out at 130 and 100 °C,
afforded 91% and 50% yields respectively (Table 1, entries
18, 19). Therefore, the optimal temperature was 130 °C.
With the optimized conditions in hand, a broad range of
substituted disulfides were subjected to reaction with 2‐
phenylpropanal. The results are summarized in Table 2.
TABLE 2 Synthesis of aryl alkyl sulfides from the reaction of diaryl disulfides and 2‐phenylpropanal in the presence of morpholinea
Entry
Disulfide
Aryl alkyl sulfide
Time (h)
Yieldb (%)
1
9
91
2
3
4
8
8
92
89
87
12
5
6
12
11
86
88
7
8
13
8
85
81
aReaction conditions: disulfide (0.5 mmol), 2‐phenylpropanal (0.5 mmol), morpholine (0.5 mmol), K2CO3 (1.5 mmol) in DMF (1 ml) at 130 °C.
bIsolated yield.

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SHAIKHI SHAHIDZADEH ET AL.
To our satisfaction, diaryl disulfides coupled well with
K2CO3 (1.5 mmol) were added and stirring was continued
at 130 °C. The results are listed in Table 3.
2‐phenylpropanal, providing the desired products in
good yields. With regards to the electronic effects, it
was found that the reaction of 2‐phenylpropanal with
substituted disulfides bearing either electron‐donating
or electron‐withdrawing groups gave the respective sul-
fide products in excellent yields; although the reaction
times are slightly higher in the case of electron‐
withdrawing groups (Table 2, entries 4–7). For instance,
the sulfide product was isolated within 8 hr in 92% yield,
when 1,2‐di‐p‐tolyldisulfane was used in reaction with 2‐
phenylpropanal (Table 2, entry 2), while 1,2‐bis(4‐
chlorophenyl)disulfane reacted under optimized condi-
tions, providing the desired product in 87% after 12 hr
(Table 2, entry 4). Under the same conditions, 1,2‐di‐o‐
tolyldisulfane also afforded the desired 1‐(phenylethyl)
(o‐tolyl)sulfane in excellent yield (Table 2, entry 3), indi-
cating that the yields were not affected by steric hin-
drance. 1,2‐bis(2‐chlorophenyl)disulfane could also
afford the corresponding products in 86% yields after
12 hr (Table 2, entry 5). Although diaryl disulfanes
furnished good yield of the sulfide products, aliphatic
ones did not provide product, may be due to the lower
sustainability of the radical species (RS. vs ArS.).
Finally, to illustrate the potential practical application
of the present protocol, the model reaction was carried
out using the same conditions as the standard assay con-
ditions, except that the reaction was scaled up using 1.0
gram of the disulphide substrate. To our delight, excellent
results was still obtained in this case (Scheme 2).
Cyanodithioformate (I) has been recently applied in
our group for conversion of organic halides to
disulfides.[21] After gaining success in thioetherification
reaction using disulfides, in the continued effort to
develop efficient protocols, we decided to investigate the
one‐pot synthesis of aryl alkyl sulfides from 2‐
phenylpropanal and aryl halides in the presence of
cyanodithioformate (I) as sulfur transfer reagent.
It is worth noting that aryl iodides with both electron‐
donating and electron‐withdrawing groups underwent
smooth coupling and delivered the corresponding prod-
ucts in good to excellent yields. The reaction of
iodobenzene with chloro substituent was found to be
chemoselective and produced the chloro‐functionalized
product in 78% yield (Table 3, entry 5). As well as aryl
iodides, aryl bromides bearing electron‐withdrawing and
electron‐donating groups were also utilized for the syn-
thesis of aryl alkyl sulfides, generating high yields
(Table 3, entries 6–11). We also studied the applicability
of the method for the reaction of aryl chlorides. In this
line, reaction of chlorobenzene with the catalytic system
at 130 °C was studied. The results showed that the reac-
tion did not proceed and starting material was isolated
intact after the appropriate reaction time. Having success-
fully established the reactivity of aryl halides in
thioetherification reactions, further investigation was
then carried out using alkyl halides. In this way, in the
absence of CuI, alkyl halides were treated with a mixture
of CS2 and KCN in DMF at 60 °C for appropriate reaction
times. After complete consuming of alkyl halide and for-
mation of the corresponding disulfide, 2‐phenylpropanal
(0.5 mmol), morpholine (0.5 mmol) and K2CO3
(1.5 mmol) were added and the reaction temperature
was adjusted to 130 °C. We observed that, despite the for-
mation of the corresponding disulfide in the first step,
with the addition of aldehyde and morpholine, there
was no reaction, and the aldehyde remained intact.
Since the formyl group does not appear in the product
structure, we first suspected that a radical process might
be presumably involved in the reaction system. In order
to gain more information about the reaction mechanism,
some control experiments were performed. When 2,2,6,6‐
tetramethyl‐1‐piperidinyloxy (TEMPO) or 2,6‐ditert‐
butyl‐4‐methylphenol (BHT) as radical inhibitors, was
employed in the model reaction, the reaction was obvi-
ously inhibited (Scheme 3). This observation implied that
the reaction presumably underwent a radical pathway.
Based on the aforementioned results and the control
experiments, a possible mechanism is proposed in
Scheme 4. Initially, diaryldisulfane can dissociate at high
temperature to generate free radical ArS•, which can trap
the H radical of 2‐phenylpropanal to form an acyl radical.
Then, the resulting acyl radical decomposes and gener-
ates an alkyl radical by releasing of CO. The obtained
alkyl radical then reacts with PhSSPh to yield aryl alkyl
sulfide and free radical PhS•.
For this purpose, a mixture of CS2 (1.2 mmol) and KCN
(1.1 mmol) in DMF (1 mL) was stirred at room temperature
for 15 min. Next, aryl halide (1.0 mmol) and CuI (20 mol%)
were added to the stirred mixture and the reaction temper-
ature was elevated to 120 °C. After complete consuming of
aryl halide and formation of diphenyl disulfide, 2‐
phenylpropanal (0.5 mmol), morpholine (0.5 mmol) and
Since the reaction is slow in the absence of
morpholine, we assume that the morpholin extracts the
generated thiol in the second step by forming the salt,
SCHEME 2 Large scale synthesis

SHAIKHI SHAHIDZADEH ET AL.
5 of 8
TABLE 3 Synthesis of aryl alkyl sulfides from the reaction of aryl halides and 2‐phenylpropanal catalyzed by CuI in the presence of KCN/
a
CS2
Entry
Aryl halide
Aryl alkyl sulfide
Time (h)
Yieldb (%)
1
10
82
2
3
9
7
83
81
4
5
6
7
8
9
9
11
15
14
14
13
83
78
80
78
77
86
10
11
18
16
79
70
aReaction conditions: First step: CS2 (1.2 mmol) and KCN (1.1 mmol) in DMF (1 ml) was stirred at room temperature for 15 min followed by addition of Ar‐X
(1.0 mmol), CuI (0.2 mmol) and heating at 120 °C until the starting aryl halide was consumed; Second step: after formation of the corresponding disulfide, 2‐
phenylpropanal (0.5 mmol), morpholine (0.5 mmol) and K2CO3 (1.5 mmol) were added and the reaction temperature was adjusted to 130 °C.
bIsolated yield.

6 of 8
SHAIKHI SHAHIDZADEH ET AL.
SCHEME 3 Control experiments
TLC, the contents were brought to room temperature,
diluted with H2O (1 ml) and extracted with n‐hexane/
ethyl acetate (1:1, 4 × 1 ml). The solvent was then evap-
orated and the crude product was purified by silica‐gel
column chromatography using n‐hexane as eluent to
give the pure products in good to excellent yields
(Table 2).
4.2 | General procedure for preparation of
aryl alkyl sulfides from aryl halides
KCN (1.1 mmol, 0.07 g) and CS2 (1.2 mmol, 0.07 ml) were
added to a flask containing DMF (1 ml) at room temper-
ature. After 15 min, aryl halide (1.0 mmol, 0.11 ml) and
CuI (20 mol%, 0.038 g) were added and the reaction mix-
ture stirred at 120 °C. The progress of the reaction was
followed by TLC analysis. After complete consuming of
aryl halide and formation of the corresponding disulfide,
2‐phenylpropanal (0.5 mmol), morpholine (0.5 mmol)
and K2CO3 (1.5 mmol) were added and the reaction tem-
perature was adjusted to 130 °C. Upon reaction comple-
tion, the mixture was cooled to room temperature,
diluted with H2O (1 ml) and extracted with n‐hexane/
ethyl acetate (1:1, 4 × 1 ml). The combined organic
extracts were concentrated and the residue purified by sil-
ica gel column chromatography using n‐hexane as eluent
to give the pure product (Table 3).
SCHEME 4 Proposed mechanism
so, shift the equilibrium to the right and increase the rate
of reaction.
3 | CONCLUSIONS
In conclusion, a novel and interesting procedure for the
construction of aryl alkyl sulfides, has been developed for
the first time through the sequential sulfenylation and
decarbonylation of 2‐phenylpropanal as coupling partner.
A variety of aromatic disulfides were used efficiently and
the desired sulfides were obtained in good to excellent
yields. Besides, thioarylation and decarbonylation of 2‐
phenylpropanal from aryl halides in the presence of CuI
and cyanodithioformate (generated in situ by stirring
KCN and CS2 in DMF), via a process which is free from
the foul smell of thiol, is described. Simple and one‐pot
procedure, easily available reagents, normal atmospheric
conditions and high yields are the other advantages of the
present system.
ACKNOWLEDGEMENTS
We thank the Persian Gulf University Research Council
for support of this study.
ORCID
Najmeh Nowrouzi https://orcid.org/0000-0002-9734-981X
4 | EXPERIMENTAL SECTION
4.1 | General procedure for preparation of
aryl alkyl sulfides from disulfides
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How to cite this article: Shaikhi Shahidzadeh E,
Nowrouzi N, Abbasi M. Utilizing 2‐phenylpropanal
as coupling partner for C‐S bond formation via
sequential thioarylation and decarbonylation
process: A novel strategy for the synthesis of aryl
alkyl sulfides. Appl Organometal Chem. 2019;e5211.
https://doi.org/10.1002/aoc.5211
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SUPPORTING INFORMATION
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