CuI-catalyzed tandem synthesis of thioethers using aryl halides, electron-deficient alkenes, and sodium iso-propyl xanthogenate

Article abstract of DOI:10.1002/aoc.5553

A ligand-free, CuI-catalyzed protocol was developed for the one-step preparation of Michael adducts of aromatic thiols in high yields by reacting a mixture of an aryl halide and an electron-deficient alkene with sodium iso-propyl xanthogenate.

Full text of DOI:10.1002/aoc.5553

Received: 21 October 2019
DOI: 10.1002/aoc.5553
Revised: 2 January 2020
Accepted: 15 January 2020
C O M M U N I C A T I O N
CuI-catalyzed tandem synthesis of thioethers using aryl
halides, electron-deficient alkenes, and sodium iso-propyl
xanthogenate
Mohammad Abbasi
| Najmeh Nowrouzi
| Rahimeh Khezri
Department of Chemistry, Faculty of
Sciences, Persian Gulf University,
Bushehr, 75169, Iran
A ligand-free, CuI-catalyzed protocol was developed for the one-step prepara-
tion of Michael adducts of aromatic thiols in high yields by reacting a mixture
of an aryl halide and an electron-deficient alkene with sodium iso-propyl
xanthogenate.
Correspondence
Mohammad Abbasi, Department of
Chemistry, Faculty of Sciences, Persian
Gulf University. Bushehr 75169, Iran.
Email: abbassi@pgu.ac.ir
K E Y W O R D S
aryl halide, CuI, sodium iso-propyl xanthogenate, thia-Michael addition
Funding information
Persian Gulf University Research Council;
Iran National Science Foundation, Grant/
Award Number: 96009857
1 | INTRODUCTION
of their oxidizing tendency, few aryl mercaptans are com-
mercially available[14] and they should be primarily syn-
Thioether functionality is an important motif found in
a large number of natural products and biologically
thesized from aryl halides via a few malodorous
procedures.
interesting compounds.[1]
A
variety of bioactive
The conjugate addition of aryl mercaptans to
electron-deficient alkenes as an efficient strategy for pre-
paring aryl alkyl thioethers has been widely studied in
organic synthesis.[13] These studies have been mainly
focused on finding new catalysts and optimizing reaction
conditions.[13] As mentioned earlier, aryl mercaptans are
rare, smelly, and unpleasant chemicals. To overcome
such drawbacks, researchers have developed alternative
protocols for preparing thia-Michael adducts by in situ
generation of aryl thiols using different strategies. In this
regard, electron-deficient alkenes have been treated with
aryl sulfonyl chloride together with Zn,[15] or diaryl dis-
ulfides along with [BnEt3N]2MoS4,[16] or a reducing
reagent such as In,[17] InI,[18] Zn,[19] Se,[20] Sm,[21] Fe,[22]
or PPh3.[23] Here we introduce an efficient ligand-free
CuI-catalyzed one-step synthesis of thia-Michael adducts
of aryl mercaptans by treating a mixture of an aryl halide
and an electron-deficient alkene with sodium iso-propyl
xanthogenate in dimethylformamide (DMF) at 110ꢀC
(Scheme 1).
thioethers have been studied as drug candidates against
drug-resistant bacteria,[2] HIV infection,[3] allergies,[4]
asthma,[4] coronary artery disease,[4] schizophrenia,[5]
bipolar disorder,[5] major depressive disorder,[5] and so
on.[6] Synthetically, they are precursors of chiral sulfox-
ides, which are useful tools in asymmetric carbon–
carbon and carbon–heteroatom bond formation.[7] They
can be oxidized to sulfones for stabilizing a radical or
anion on the α-carbon atom.[8] Removal of the sulfur
moiety after the completion of the procedure by reduc-
tive desulfurization provides access to sulfur-free
products.[9]
Alkyl aryl thioethers can be prepared by cross-
coupling of aliphatic thiols with aryl derivatives bearing a
leaving group catalyzed by transition metals[10] or by
treating aryl mercaptans with a variety of reactants,
including alkyl halides,[11] alkenes,[12] and electron-
deficient alkenes.[13] The use of foul-smelling thiols is a
major difficulty of these strategies. Furthermore, because
Appl Organometal Chem. 2020;e5553.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5553

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ABBASI ET AL.
but similar reactions in polyethylene glycol-200
(PEG-200), dimethyl sulfoxide (DMSO), and toluene gave
it in 37%, 43%, 40% yields, respectively, after this period.
Also, the reactions in H2O and sodium dodecyl sulfate
(SDS) micellar medium completely failed and after the
same time period the starting iodobenzenes were recov-
ered unreacted near quantitatively for both reactions.
After choosing DMF as the solvent, we examined sev-
eral different bases. The bases Na2CO3, K2CO3, KOH,
Et3N, and NaOH did not give higher yield than NaHCO3
(Table 1, entry 1 vs. 7–12). Subsequently, by changing the
amount of NaHCO3 in the reaction, we found that an
increase in the amount of NaHCO3 reduces the reaction
time and increases the reaction yield. For example, by
increasing the amount of NaHCO3 to 4 and 6 equivalents,
the starting iodobenzene was completely consumed to
give butyl 3-(phenylthio)propanoate in 84% (within 4 hr)
and 90% (12 hr) yields, respectively. On the other hand,
decreasing the catalyst loading to 10 mol% or the reaction
temperature to 100ꢀC reduced the reaction efficiency.
Meanwhile, the reaction time or yield was not improved
SCHEME 1 One-pot, non-sequential synthesis of thia-
Michael products. DMF, dimethylformamide; EWG, electron
withdrawing group
2 | RESULTS AND DISCUSSION
To start our study, different solvents were screened for
reaction of iodobenzene (1.2 mmol), butyl acrylate
(1 mmol), and sodium iso-propyl xanthogenate
(1.3 mmol) in the presence of NaHCO3 (2 mmol) and CuI
(20 mol%) at 110ꢀC for 24 hr. The results are summarized
in Table 1.
Although none of the reactions were complete after
this period, the reaction in DMF gave the best yield
(Table 1, entry 1). It gave the desired product in 54% yield
TABLE 1 Reaction of iodobenzene, sodium iso-propyl xanthogenate, and butyl acrylate under different conditionsa
Entry
Solvent
DMF
Base/Z (mmol)
NaHCO3/2
NaHCO3/2
NaHCO3/2
NaHCO3/2
NaHCO3/2
NaHCO3/2
Na2CO3/2
K2CO3/2
CuX/Y (mol%)
CuI/20
t (hr)
24
24
24
24
24
24
24
24
24
24
24
17
12
12
24
24
15
16
T (ꢀC)
110
110
110
110
110
110
110
110
110
110
110
110
110
120
100
110
110
110
Yield (%)
1
2
3
3
4
54
43
–
DMSO
H2O
CuI/20
CuI/20
SDS/H2O
PEG-200
PhCH3
DMF
CuI/20
–
CuI/20
37
40
54
53
45
50
52
84
90
87
80
55
85
79
CuI/20
5
CuI/20
6
DMF
CuI/20
7
DMF
Et3N/2
CuI/20
8
DMF
NaOH/2
CuI/20
9
DMF
KOH/2
CuI/20
10
11
12
13
14
15
16
DMF
NaHCO3/4
NaHCO3/6
NaHCO3/6
NaHCO3/6
NaHCO3/6
NaHCO3/6
NaHCO3/6
CuI/20
DMF
DMF
CuI/20
CuI/20
DMF
CuI/20
DMF
CuI/10
DMF
CuCl/20
Cu (OAc)2/20
DMF
DMF, dimethylformamide; DMSO, dimethyl sulfoxide; PEG-200, polyethylene glycol; SDS, sodium dodecyl sulfate.
aReaction conditions: PhI (1.2 mmol), sodium iso-propyl xanthogenate (1.3 mmol), butyl acrylate (1 mmol), solvent (2 ml).

SYNTHESIS OF ARYL THIOETHERS USING NON-THIOLIC PRECURSORS
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by elevation of temperature from 110 to 120ꢀC or with
increasing catalyst loading to 30 mol%. With the optimal
reaction conditions in hand, we proceeded to investigate
the scope of the reaction for the synthesis of thia-Michael
adducts using a range of different aryl halides and elec-
tron-deficient alkenes.
The results shown in Table 2 indicate that both aryl
iodides and bromides efficiently react with sodium iso-
propyl xanthogenate and electron-deficient alkenes under
reaction conditions to produce thia-Michael adducts in
high yields. Iodobenzene reacts completely within 12 hr,
but bromobenzene reacts more slowly and is consumed
after 19 hr. Also, both ortho- and para-iodotoluenes react
much slower than iodobenzene but in high yields. Also,
deficient alkene followed by proton capture from
bicarbonate to produce the thia-Michael adduct.
According to path B, the conjugate addition of iso-
propyl xanthogenate to alkene results in the thia-Michael
adduct 4, which subsequently undergoes basic hydrolysis
to form the aliphatic thiolate 5. On the other hand, inser-
tion of Cu into the aryl–X bond generates intermediate 1,
which under treatment with the aliphatic thiolate 5 gener-
ates intermediate 6 by replacing halide with thiolate.
Finally, a reductive elimination process regenerates CuI
catalyst and releases the thia-Michael adduct.
In order to understand the thiol intermediates
involved in the process and therefore to approve or
reject the proposed mechanisms, a reaction using
iodobenzene (1.2 mmol), butyl acrylate (1 mmol),
sodium iso-propyl xanthogenate (1.3 mmol), NaHCO3
(6 mmol), and CuI (20 mol%) in DMF at 110 oC was
conducted in the presence of C2Cl6 (1 mmol). Thiols in
the presence of C2Cl6 undergo fast oxidation to symmet-
ric disulfides.[24] The reaction in the presence of C2Cl6
gave only diphenyl disulfide and the starting butyl acry-
late was recovered unreacted from the reaction mixture
in near-quantitative yield. This finding confirms path A
and rejects path B.
para-bromotoluene
reacts
more
slowly
but
4-bromobenzonitrile reacts faster than bromobenzene.
Reactions with the participation of 2-bromopyridine
proceeded to completion more slowly than with
bromobenzene and gave lower yields of Michael
products.
We considered two reasonable pathways for the reac-
tion, marked path A and path B in Scheme 2.
According to path A, CuI undergoes oxidative addi-
tion by insertion into the aryl C–X bond to produce
Cu(III) intermediate 1. Next, this intermediate is
converted to intermediate 2 by replacing halide (X−)
with xanthogenate on Cu. This step is followed by
reductive elimination to give O-iso-propyl S-phenyl
carbonodithioate (3) along with regeneration of CuI. This
intermediate under basic hydrolysis affords aryl thiolate,
which in turn undergoes 1,4-addition to an electron-
In conclusion, we have developed conditions for a
one-step copper-catalyzed synthesis of thia-Michael
products of aromatic thiols using aryl halides, sodium
iso-propyl xanthogenate, and diverse electron-deficient
alkenes. The method is ligand-free, one-pot, one-step,
thiol-free, and simple, giving thia-Michael adducts in
good to excellent yields.
SCHEME 2 Two possible reaction pathways. Path A was confirmed by further experiments whereas path B was rejected.
EWG, electron withdrawing groups

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ABBASI ET AL.
TABLE 2 Synthesis of Michael adducts by reacting aryl halides, electron-deficient alkenes, and sodium iso-propyl xanthogenatea
Entry
ArX
Alkene
Product
T (hr)
Yield (%)
1
Butyl acrylate
12
89
2
Ethyl acrylate
12
86
3
4
5
Methyl acrylate
Acrylonitrile
12
12
12
86
85
83
Methyl vinyl sulfone
6
7
8
Ethyl acrylate
21
21
21
85
84
80
Acrylonitrile
Methyl vinyl sulfone
9
Methyl acrylate
Butyl acrylate
21
21
83
10
85
(Continues)

SYNTHESIS OF ARYL THIOETHERS USING NON-THIOLIC PRECURSORS
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TABLE 2 (Continued)
Entry
ArX
Alkene
Product
T (hr)
Yield (%)
11
Methyl vinyl sulfone
21
85
12
13
14
Acrylonitrile
Ethyl acrylate
Ethyl acrylate
20
20
17
85
85
85
15
Methyl acrylate
17
85
16
17
Butyl acrylate
Ethyl acrylate
19
19
86
86
18
19
20
Methyl acrylate
Acrylonitrile
19
19
19
85
83
81
Methyl vinyl sulfone
(Continues)

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ABBASI ET AL.
TABLE 2 (Continued)
Entry
ArX
Alkene
Product
T (hr)
Yield (%)
21
Acrylonitrile
28
83
22
23
Ethyl acrylate
28
28
84
80
Methyl vinyl sulfone
24
25
Ethyl acrylate
Acrylonitrile
24
24
82
79
aReaction conditions: aryl halide (1.2 mmol), sodium iso-propyl xanthogenate (1.3 mml), electron-deficient alkene (1 mmol), CuI (0.2 mmol), NaHCO3
(6 mmol), DMF (2 ml), 110ꢀC.
3 | EXPERIMENTAL SECTION
Ethyl 3-(phenylthio)propanoate (Table 2, entries
2 and 17): 1H NMR (400 MHz, CDCl3) δ (ppm): 7.40–7.37
(m, 2H), 7.34–7.28 (m, 2H), 7.25–7.21 (m, 1H), 4.16
(q, J = 7.1 Hz, 2H), 3.19 (t, J = 7.4 Hz, 2H), 2.64
(t, J = 7.4 Hz, 2H), 1.27 (t, J = 7.1 Hz, 3H); 13C NMR
(100 MHz, CDCl3) δ (ppm): 171.7, 135.3, 130.1, 129.0,
126.5, 60.7, 34.42, 29.0, 14.2.
General procedure: An aryl halide (1.2 mmol), a Michael
acceptor (1 mmol), CuI (0.2 mmol), and NaHCO3
(6 mmol) were added to a mixture of sodium iso-propyl
xanthogenate (1.3 mmol) in DMF (2 ml). The reaction
mixture was stirred at 110ꢀC until the aryl halide was
consumed. After that, the mixture was diluted with H2O
(0.5 ml) and extracted with 1:1 n-hexane/ethyl acetate
(4 × 1 ml). The organic extracts were combined, concen-
trated, and purified by chromatography on silica gel
using n-hexane or a suitable mixture of n-hexane/EtOAc
as eluent to obtain pure product.
Methyl 3-(phenylthio)propanoate (Table 2, entries
1
3 and 18): H NMR (400 MHz, CDCl3) δ (ppm) 7.40–7.35
(m, 2H), 7.33–7.27 (m, 2H), 7.23–7.17 (m, 1H), 3.67
(s, 3H), 3.17 (t, J = 7.1 Hz, 2H), 2.63 (t, J = 7.1 Hz, 2H);
13C NMR (100 MHz, CDCl3) δ (ppm) 172.3, 135.4, 130.3,
129.2, 126.7, 51.9, 34.4, 29.2.
The NMR spectra of products are shown in the
supporting information file.
3-(Phenylthio)propanenitrile (Table 2, entries 4 and
19): 1H NMR (400 MHz, CDCl3) δ (ppm): 7.47–7.44
(m, 2H), 7.40–7.30 (m, 3H), 3.15 (t, J = 7.2 Hz, 2H), 2.62
(t, J = 7.2 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ (ppm):
133.3, 131.5, 129.5, 127.9, 118.2, 30.3, 18.4.
Butyl 3-(phenylthio)propanoate (Table 2, entries
1 and 16): 1H NMR (400 MHz, CDCl3) δ (ppm):
7.41–7.39 (m, 2H), 7.35–7.31 (m, 2H), 7.26–7.22
(m, 1H), 4.12 (t, J = 6.7 Hz, 2H), 3.20 (t, J = 7.4 Hz,
2H), 2.66 (t, J = 7.4 Hz, 2H), 1.67–1.60 (m, 2H),
1.45–1.36 (m, 2H), 0.96 (t, 3H); 13C NMR (100 MHz,
CDCl3) δ (ppm):171.9, 135.3, 130.1, 129.9, 126.6, 64.7,
34.5, 30.6, 29.1, 19.2, 13.7.
(2-(Methylsulfonyl)ethyl)(phenyl)sulfane (Table 2,
1
entries 5 and 20): H NMR (300 MHz, CDCl3) δ (ppm):
7.46–7.31 (m, 5H), 3.40–3.33 (m, 2H), 3.31–3.23 (m, 2H),
2.97 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm): 133.3,
130.7, 129.5, 127.6, 54.5, 41.4, 26.5.

SYNTHESIS OF ARYL THIOETHERS USING NON-THIOLIC PRECURSORS
7 of 9
1
Ethyl 3-(o-tolylthio)propanoate (Table 2, entry 6): H
NMR (400 MHz, CDCl3) δ (ppm): 7.37–7.35 (m, 1H),
7.23–7.14 (m, 3H), 4.18 (q, J = 7.1 Hz, 2H), 3.19
(t, J = 7.4 Hz, 2H), 2.67 (t, J = 7.4 Hz, 2H), 2.42 (s, 3H),
1.30 (t, J = 7.1 Hz, 3H), 13C NMR (100 MHz, CDCl3) δ
(ppm): 171.8, 138.4, 134.6, 130.3, 129.1, 126.5, 126.4, 60.8,
34.3, 28.3, 20.5, 14.2.
Methyl 3-((4-cyanophenyl)thio)propanoate (Table 2,
entry 15): 1H NMR (400 MHz, CDCl3) δ (ppm) 7.54
(d, J = 8.4 Hz, 2H), 7.32 (d, J = 8.4 Hz, 2H), 3.72 (s, 3H),
3.24(t, J = 7.2 Hz, 2H), 2.68 (t, J = 7.1 Hz, 2H); 13C NMR
(100 MHz, CDCl3) δ (ppm) 171.9, 143.8, 132.6, 127.7,
118.9, 109.0, 52.3, 33.8, 27.3.
1
3-(p-Tolylthio)propanenitrile (Table 2, entry 21): H
3-(o-Tolylthio)propanenitrile (Table 2, entry 7): 1H
NMR (400 MHz, CDCl3) δ (ppm): 7.39–7.36 (m, 1H),
7.29–7.20 (m, 3H), 3.14 (t, J = 7.2 Hz, 2H), 2.61
(t, J = 7.2 Hz, 2H), 2.47 (3, 3H); 13C NMR (100 MHz,
CDCl3) δ (ppm): 139.6, 132.4, 130.8, 130.7, 127.6, 126.8,
118.1, 29.3, 20.5, 18.1.
NMR (400 MHz, CDCl3) δ (ppm): 7.37 (d, J = 7.7 Hz,
2H), 7.19 (d, J = 7.7 Hz, 2H), 3.10 (t, J = 7.3 Hz, 2H), 2.59
(t, J = 7.3 Hz, 2H), 2.38 (s, 3H), 13C NMR (100 MHz,
CDCl3) δ (ppm): 138.4, 132.4, 130.4, 129.5, 118.3, 31.0,
21.3, 18.4.
Ethyl 3-(p-tolylthio)propanoate (Table 2, entry 22): 1H
NMR (400 MHz, CDCl3) δ (ppm): 7.31 (d, J = 7.9 Hz,
2H), 7.13 (d, J = 7.9 Hz, 2H), 4.15 (q, J = 7.2 Hz, 2H),
3.14 (t, J = 7.4 Hz, 2H), 2.61 (t, J = 7.4 Hz, 2H), 2.34
(s, 3H), 1.27 (t, J = 7.2 Hz, 3H), 13C NMR (100 MHz,
CDCl3) δ (ppm): 171.8, 136.7, 131.3, 131.0, 129.7, 60.6,
34.5, 29.7, 21.0, 14.2.
(2-(Methylsulfonyl)ethyl)(o-tolyl)sulfane (Table 2,
1
entry 8): H NMR (300 MHz, CDCl3) δ (ppm): 7.39–7.34
(m, 1H), 7.28–7.19 (m, 3H), 3.37–3.22 (m, 4H), 2.97
(s, 3H), 2.44 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm):
139.0, 132.6, 130.8, 129.8, 127.4, 126.9, 54.3, 41.3, 25.5,
20.5.
Butyl 3-(p-tolylthio)propanoate (Table 2, entry 10):
1H NMR (400 MHz, CDCl3) δ (ppm): 7.32 (d, J = 8.1 Hz,
2H), 7.14 (d, J = 8.1 Hz, 2H), 4.10 (t, J = 6.7 Hz, 2H),
3.14 (t, J = 7.4 Hz, 2H), 2.62 (t, J = 7.4 Hz, 2H), 2.35
(s, 3H), 1.66–1.59 (m, 2H), 1.44–1.35 (m, 2H), 0.97
(t, J = 7.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ
(ppm): 172.1, 137.0, 131.5, 131.2, 130.0, 64.7, 34.7, 30.8,
29.9, 21.2, 19.3, 13.9.
Ethyl 3-(pyridin-2-ylthio)propanoate (Table 2, entry
24): H NMR (400 MHz, CDCl3) δ (ppm): 8.45–8.44 (m,
1
1H), 4.527.48 (m, 1H), 7.19 (d, J = 8.0 Hz, 1H), 7.02–6.99
(m, 1H), 4.19 (q, J = 7.1 Hz, 2H), 3.46 (t, J = 7.1 Hz, 2H),
2.80 (t, J = 7.1 Hz, 2H), 1.29 (t, J = 7.1 Hz, 3H); 13C NMR
(100 MHz, CDCl3) δ (ppm): 172.1, 158.2, 149.4, 135.9,
122.4, 119.5, 60.6, 34.7, 24.9, 14.1.
3-(Pyridin-2-ylthio)propanenitrile (Table 2, entry 25):
1H NMR (400 MHz, CDCl3) δ (ppm): 8.47–8.45 (m, 1H),
7.57–7.53 (m, 1H), 7.23 (d, J = 8.0 Hz, 1H), 7.08–7.05
(m, 1H), 3.46 (t, J = 7.1 Hz, 2H), 2.90 (t, J = 7.1 Hz, 2H),
13C NMR (100 MHz, CDCl3) δ (ppm): 156.6, 149.6, 136.3,
122.7, 120.0, 118.7, 25.6, 18.8.
(2-(Methylsulfonyl)ethyl)(p-tolyl)sulfane (Table 2,
1
entries 11 and 23): H NMR (300 MHz, CDCl3) δ (ppm):
7.33 (dd, J = 8.2, 1.2 Hz, 2H), 7.17 (d, J = 7.9 Hz, 2H),
3.33–3.17 (m, 4H), 2.93 (s, 3H), 2.36 (s, 3H); 13C NMR
(75 MHz, CDCl3) δ (ppm):138.0, 131.5, 130.3, 129.6, 54.4,
41.3, 27.2, 21.1.
3-((4-Fluorophenyl)thio)propanenitrile (Table 2, entry
12): 1H NMR (400 MHz, CDCl3) δ (ppm): 7.50–7.46
(m, 2H), 7.10–7.06 (m, 2H), 3.10 (t, J = 7.2 Hz, 2H), 2.60
(t, J = 7.2 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ (ppm):
164.1, 161.6, 134.8, 134.7, 128.2, 128.16, 118.0, 116.8,
116.6, 77.5, 77.2, 76.8, 31.4, 18.4.
Ethyl 3-((4-fluorophenyl)thio)propanoate (Table 2,
entry 13): 1H NMR (400 MHz, CDCl3) δ (ppm): 7.42–7.38
(m, 2H), 7.02 (t, J = 8.7 Hz, 2H), 4.15 (q, J = 7.1 Hz, 2H),
3.12 (t, J = 7.4 Hz, 2H), 2.59 (t, J = 7.4 Hz, 2H), 1.26
(t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ (ppm):
171.7, 163.4, 160.9, 133.4, 133.3, 130.1, 130.1, 116.3, 116.0,
60.7, 34.5, 30.4, 14.2.
ACKNOWLEDGEMENTS
We thank the Persian Gulf University Research Council
and Iran National Science Foundation (INSF grant
no.96009857) for support of this work.
ORCID
Mohammad Abbasi https://orcid.org/0000-0002-0505-
7159
Najmeh Nowrouzi https://orcid.org/0000-0002-9734-
981X
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entry 14): 1H NMR (400 MHz, CDCl3) δ (ppm):7.58
(d, J = 8.4 Hz, 2H), 7.36 (d, J = 8.4 Hz, 2H), 4.20
(q, J = 7.2 Hz, 2H), 3.29 (t, J = 7.3 Hz, 2H), 2.71
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(100 MHz, CDCl3) δ (ppm): 171.2, 143.5, 132.3, 127.2,
118.7, 108.7, 61.0, 33. 7, 27.0, 14.1.

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SUPPORTING INFORMATION
Additional supporting information may be found online
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How to cite this article: Abbasi M, Nowrouzi N,
Khezri R. CuI-catalyzed tandem synthesis of
thioethers using aryl halides, electron-deficient
alkenes, and sodium iso-propyl xanthogenate. Appl
Organometal Chem. 2020;e5553. https://doi.org/10.
1002/aoc.5553