Direct Assembly of Polysubstituted Furans via C(sp3)?H Bond Functionalization by Using Dimethyl Sulfoxide as a Dual Synthon

Article abstract of DOI:10.1002/adsc.201801429

An unusual I₂-mediated triple C(sp³)?H functionalization reaction between aryl methyl ketones and dimethyl sulfoxide to form polysubstituted furans has been developed. In this transformation, dimethyl sulfoxide functions as a dual synthon via C(sp³)?H functionalization with formation of two C?C bonds, one C?O bond, and one C?S bond in a one-step process. Iodine is crucial as promoter of the reaction, by which a number of ketones could be converted easily into 2,4,5-trisubstituted furans. This provides an extremely simple and expeditious approach to high-value-added, biologically significant O-heterocycles. Based on preliminary experiments, a plausible mechanism is proposed. (Figure presented.).

Full text of DOI:10.1002/adsc.201801429

Title: Direct Assembly of Polysubstituted Furans via C(sp3)-H Bonds
Functionalization Reaction Using Dimethyl Sulfoxide as a Dual
Synthon
Authors: Yufeng Liu, Yuqun Hu, Zhongzhong Cao, Zhan Xi, Wei-Ping
Luo, Liu Qiang, and Can-Cheng Guo
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
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the VoR from the journal website shown below when it is published
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content of this Accepted Article.
To be cited as: Adv. Synth. Catal. 10.1002/adsc.201801429
Link to VoR: http://dx.doi.org/10.1002/adsc.201801429

Advanced Synthesis & Catalysis
10.1002/adsc.201801429
FULL PAPER
DOI: 10.1002/adsc.201
3
Direct Assembly of Polysubstituted Furans via C(sp )–H Bond
Functionalization by Using Dimethyl Sulfoxide as a Dual
Synthon
a
a
a
a
a
a
Yufeng Liu , Yuqun Hu , Zhongzhong Cao , Xi Zhan , Weiping Luo , Qiang Liu *,
a
Cancheng Guo *
a
College of Chemistry and Chemical Engineering, Advanced Catalytic Engineering Research Center of the Ministry of
Education, Hunan University, Changsha 410082, China
E-mail: fqiangliu@qq.com and ccguo@hnu.edu.cn
Received:
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.
3
Abstract. An unusual
I
2
-mediated triple C(sp )−H converted easily into 2,4,5-trisubstituted furans. This
functionalization reaction between aryl methyl ketones and provides an extremely simple and expeditious approach to
dimethyl sulfoxide to form polysubstituted furans has been high-value-added, biologically significant O-heterocycles.
developed. In this transformation, dimethyl sulfoxide Based on preliminary experiments, a plausible mechanism
3
functions as a dual synthon via C(sp )−H functionalization is proposed.
with formation of two C–C bonds, one C–O bond, and one
C–S bond in a one-step process. Iodine is crucial as promoter Keywords: ketones; DMSO; 2,4,5-trisubstituted furans;
3
of the reaction, by which a number of ketones could be
C(sp )−H functionalization; dual synthon
functionalization reaction of aryl methyl ketones and
rongalite. The process employed rongalite as a C1
Introduction
[10]
unit and DMSO as an SMe unit (Scheme 1d).
Although various methods have been reported for
Polysubstituted furans make up an important class
of heterocycles, appearing as key structural units in constructing the furan scaffold, a direct synthesis of
3
polysubstituted furans through multiple C(sp )–H
natural
products,
pharmaceuticals,
and
agrochemicals.[
1]
They also represent useful
functionalizations with more readily available
intermediates in synthetic chemistry and materials materials is still required.
science,[ and, as a consequence, extensive efforts
2]
have been made towards the construction of the furan
skeleton. The classical methods such as the
Paal−Knorr [ and Feist−Benary
3]
[4]
furan syntheses
provide rapid access to substituted furans from
dicarbonyl compounds. During the past years, the
direct functionalization of C–H bonds for the
construction of new C–C bonds has been one of the
most important strategies in the field of modern
chemistry research.[ Several elegant advances have
5]
3
shed light on methods involving direct C(sp )–H bond
functionalization to construct the furan scaffold. In
this context, strategies for exploring cross-coupling of
aryl methyl ketones with alkene- or alkyne-containing
[
6]
compounds have been extensively studied.
Significantly, the Hajra group reported a Cu-mediated
cross-coupling of aryl methyl ketones with β-
[
7]
nitrostyrene to synthesize furans (Scheme 1a).
Scheme 1 Selective Examples of Furan Synthesis via
Antonchick’s group demonstrated a furan synthesis
3
C(sp )−H Bond Functionalization
3
via Cu-catalyzed C(sp )–H functionalization of aryl
[8]
methyl ketones with alkynes (Scheme 1b). Lei and
co-workers reported an efficient furan synthesis
Dimethyl sulfoxide (DMSO) is one of the most
commonly used, inexpensive, and less toxic solvents
method by annulation of alkynes with 1,3-diketones
Scheme 1c).[ Recently, the Wu group reported an
9]
(
I
[11]
3
in chemical transformations.
In the past decades,
2
/Cu(NO
3
)
2
·3H
2
O mediated triple C(sp )–H bond
1
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Advanced Synthesis & Catalysis
10.1002/adsc.201801429
DMSO has also been widely utilized as a single as oxone, (NH ) S O , TBHP, H O and O were also
4
2
2
8
2
2
2
[
12]
[13]
synthon as a source for units such as O,
Me,
applied in this reaction, K
2
S
2
O
8
afforded the best
SMe,[
14]
SOMe,
[15]
SO
Me,
[16]
MeSCH
for incorporation into target
,[17]
2
2
result (entries 6-10). Increasing the temperature did
not improve the yield (entry 11). At low temperature,
the acetophenone could not fully converted to the
product (entry 12). It is worth noting that the yield of
18]
,[ and CN
[19]
MeSOCH
2
molecules. However, to the best of our knowledge,
the application of DMSO as a dual synthon in the
construction of the furan scaffold has not yet been
reported.[
20]
Herein, we would like to report a product was decreased when changing the amount of
3
transition-metal-free
efficient
C(sp )–H
DMSO and K
2
S
2
O (entries 13-16).
8
functionalization reaction between alkyl ketones and
DMSO, illustrating an efficient example of achieving
polysubstituted furans in one step under mild
conditions (Scheme 1e).
With the optimized reaction conditions in hand
(
Table 1, entry 1), we explored the scope of the
3
C(sp )-H functionalization protocol with the
(
hetero)aryl methyl ketones. The results are
summarized in Scheme 2. Promoted by I , almost all
2
of the aryl methyl ketones are effective to form the
polysubstituted furans under the standard conditions.
As shown in Scheme 2, both electron-withdrawing
and -donating substituted groups in benzene ring were
Results and Discussion
We initiated our studies with acetophenone (1a
as the model substrate to screen the optimal
reaction conditions and the results were
summarized in Table 1. The combination of I and
in DMSO at 120 °C was found to be the
best reaction conditions for this I -mediated
)
well tolerated under the standard conditions, such as
t
Me, Bu, OMe, SMe, CF
3
and NO groups (Scheme
2
2
2
， 3a-3l). To our delight, aryl methyl ketones
K
2
S
2
O
8
bearing halo substituted groups such as chloro, and
bromo could also be converted into the desired
corresponding furans (Scheme 2, 3m-3r), which
provides the potential for further functionalization via
cross coupling. Especially, highly
2
oxidation process (entry 1). Other reaction factors
were investigated and the results were listed in
entries 2-16. The furan product was also obtained
with other catalysts but I was proving to be
2
optimal (entries 2-5). Other various oxidants, such
Table 1. Optimization of Reaction Conditions.a)
Entry Catalyst Oxidant Temp (℃) Yield (%) b
1
2
3
4
5
6
7
8
9
I
2
K
K
K
K
K
2
2
2
2
2
S
S
S
S
S
2
2
2
2
2
O
O
O
O
O
8
8
8
8
8
120
120
120
120
120
120
120
120
120
120
130
100
120
120
120
120
84
83
TBAI
KI
53
TBAB
TBAC
61
45
I
I
I
I
I
I
I
I
I
I
I
2
2
2
2
2
2
2
2
2
KHSO
(NH
TBHP
5
32
4
)
2
S
2
O
8
19
trace
trace
trace
78
2 2
H O
1
0
1
2
O
2
1
1
K
K
K
K
K
K
2
S
S
S
S
S
S
2
O
O
O
O
O
O
8
2
2
2
2
2
2
8
8
8
61
1
1
1
3c
4d
5e
53
65
2
2
2
2
2
2
8
8
71
1 f
6
59
Scheme 2 Reaction scope of different methyl ketones.
Reaction conditions: acetophenone (1, 0.5 mmol), DMSO
a)
Reaction conditions: acetophenone (1a, 0.5 mmol),
DMSO (2.0 mL), catalyst (30 mol %), oxidant (1 mmol)
(
2a, 2 mL), I
2
(0.15 mmol), K
2
S
2
O
8
(1.0 mmol) for 8 h.
b)
c)
d)
for 8 h. Isolated yield. DMSO (1.0 mL). DMSO (3.0
mL),
Isolated yield.
e)
f)
2 2
I (10 mol %), I (50 mol %).
2
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Advanced Synthesis & Catalysis
10.1002/adsc.201801429
sterically hindered o-substituted aryl methyl chloro-2hydroxyphenyl-)ethan-1-one, 1.5 mmol I
ketones furnished the desired furan products and 20 mmol K S O were heated in 60 mL
2
2
2
8
o
smoothly (Scheme 2, 3b, 3e, 3i, 3k, 3m, 3p). DMSO at 120 C for 16h to obtain 3w with 56%
Moreover, methyl ketone containing naphthyl and
thiophene could also be employed to form the
furan scaffolds without any difficulties (Scheme
yield
(1265.6
mg)
by
flash
column
chromatography on silica. Compound 3a was also
prepared in 73% isolated yield at 10 mmol scale
by following the similar experimental procedure.
In order to have a deeper understanding of the
role of molecular-iodine and to get some insight
into the mechanism, several control experiments
were conducted (Scheme 5). When 2 equivalents
of the radical inhibitor TEMPO (2,2,6,6-
tetramethyl-1-piperidinyloxy) was added, product
2
,
3s and 3t). However, the alkyl methyl ketones
like 3,3-dimethylbutan-2-one did not work in the
present reaction system (3u).
H-Chromen-4-one is a key core component in
many synthetic drugs and natural products with
4
[
21]
various biological activities. Intriguingly, under
the standard conditions, substituted o-
hydroxyacetophenones 1v 1y underwent
intramolecular cycloaddition to give the
thiomethylated chroman-4-ones in one pot
Scheme 3). For example, o-
hydroxyacetophenone reacted with DMSO
smoothly to produce the corresponding 3-
methylthio)-4H-chromen-4-one 3v in 56% yield.
The chloro-/CH -containing
thiomethylated standard reaction condition (eq 2). In an I
chroman-4-ones were also synthesized under system, the α-iodo acetophenone ( ) potentially
similar reaction conditions (3w
3y, and 3z). Thus, generated by acetophenone, but couldn’t
this cross-coupling method provides a novel and transform to 3a under standard reaction condition
facile way to construct the valuable (eq 3). When we employed
and as the
simultaneously under standard
condition, product 3a was obtained in 75% yield
eq 4), which implied that and
-
3
a
was not obtained under standard conditions (eq
1
), which indicated that this reaction may proceed
a radical pathway. When we carried out this
(
reaction without I
the 1-phenylprop-2-en-1-one (
3% yield and couldn’t transform to 3a under
/DMSO
2
, product 3a was not obtained,
C
) was obtained in
4
C
(
3
2
A
,
A
A
C
thiomethylated chroman-4-ones from simple substrate
ortho-hydroxy-acetophenones.
(
A
C
simultaneously generated by acetophenone under
standard conditions. Furthermore, the reaction of
dimethyl (phenacyl)-sulfonium
Scheme 3. One-pot synthesis of thiomethylated 4H-
chroman-4-ones. Reaction conditions: acetophenone (1, 0.5
mmol), DMSO (2a, 2 mL), I (0.15 mmol), K S O (1.0
2 2 2 8
mmol) for 8 h. Isolated yield.
More practically, this reaction could be
performed at 10 mmol scale, which clearly
showing the potential application in organic
synthesis (Scheme 4). For example, 10mmol 1-(4-
Scheme 4 Gram-scale preparation of 3w.
Scheme 5 Control experiments
3
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Advanced Synthesis & Catalysis
10.1002/adsc.201801429
bromide
D with intermediate C
under the Conclusion
standard conditions afforded 3a in 80% yield. In
the presence of TEMPO, this reaction could not
proceed and a TEMPO-trapped compound
In summary, we have reported a novel iodine-
E
was mediated oxidative C−H functionalization
detected by GC-MS (eq 5). In addition, when following heterocyclization reaction of aryl
TEMPO was added to the reaction mixture of
methyl ketones with DMSO. The method
and DMSO, compound
was also detected, thus provides direct and efficient entry to
suggesting that the radical intermediate derived polysubstituted furans in one step by employing
from
(eq 6). Deuterium experiments were also DMSO as a C1 and sulfur methyl unit. This
D
E
a
D
carried out. By using DMSO-d6 instead, 1a protocol could be applied to prepare
underwent the coupling reaction to give 3a-d4 in polysubstituted furans and flavone thioethers
8
1% yield (eq 7), showing that the methylene and from basic starting materials under mild
sulfur methyl was from DMSO.
conditions. Furthermore, this reaction can be
conducted on a 10 mmol scale, clearly showing
On the basis of the experimental results the potential practicality of this coupling reaction
described above and previous literature in organic synthesis. On the basis of control
[
10,17c]
reports,
polysubstituted furan is proposed as shown in proposed.
Scheme 6. Initially, in the I /DMSO system, 1a
reacts with molecular iodine to form α-
iodoacetophenone (
dimethyl (phenacyl)-sulfonium iodine (
presence of dimethyl sulfide (DMS) which is
generated by the reduction of DMSO. A radical commercial suppliers were used as received unless
intermediate results from with the aid of mentioned otherwise. Products were purified by flash
. Meanwhile, the reaction of 1a with chromatography on silica gel (300-400 mesh), and
a possible reaction path for the experiments,
a
plausible reaction path is
2
A
). Then A is converted into Experimental Section
B
) in the
General Methods. Materials obtained from
F
B
K
2
S
2
O
8
1
13
1
DMSO in the presence of K
formation of 1-phenylprop-2-en-1-one (
radical addition of to enone gives the spectrometer and the chemical shifts (δ) were reported
. The intermediate transforms to in ppm relative to internal standard TMS (0 ppm) for
through single-electron transfer CDCl . The peak patterns are indicated as follows: s,
2
S
2
O
8
results in the were characterized by H NMR, and C NMR. H
C
). The NMR spectra were recorded on 400 MHz
F
C
intermediate
intermediate
G
H
G
3
(
SET [O]). An intramolecular nucleophilic singlet; d, doublet; dd, doublet of doublet; t, triplet; m,
addition cyclization results in the desired product multiplet; q, quartet; brs, broad singlet. The coupling
[
10]
13
3a
.
constants, J values, are given in Hertz (Hz). C NMR
spectra were obtained at 100 MHz and referenced to
the internal solvent signals (central peak is 77.0 ppm
1
13
Scheme 6. Possible Mechanism.
in CDCl ). Copies of H NMR and C NMR spectra
3
are provided as Supporting Information. High-
resolution mass spectra (HRMS) were measured on a
double focusing mass spectrometer with an EI source.
Typical experimental procedure for the
formation of polysubstituted furans. In a Schlenk
tube of 25 mL, acetophenone 1 (0.5 mmol, 1.0 equiv),
K
2
S
2
O
8
(1.0 mmol, 2 equiv) and I
mol%) were dissolved in DMSO (2 mL) and stirred at
20 ºC for 8 h. After completion of the reaction, the
2
(0.15 mmol, 30
1
resulting solution was cooled to room temperature;
the solution was diluted with ethyl acetate (10 mL),
washed with water (5 mL), extracted with ethyl
acetate (3×5 mL), and dried over anhydrous Na
2
SO
4
and concentrated in vacuo. The crude product was
purified by flash column chromatography on silica gel
to give the desired product.
Gram scale synthesis
A round-bottomed of 250 mL flask equipped with a
magnetic stir bar (20 mm) was charged with ortho-
hydroxyacetophenone (1w, 10 mmol), K
mmol, 2 equiv) and I (1.5 mmol, 30 mol%) were
dissolved in DMSO (60 mL) and stirred at 120 ºC for
6 h. After completion of the reaction, the resulting
2 2
S
8
O (20
2
1
solution was cooled to room temperature; the solution
4
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Advanced Synthesis & Catalysis
10.1002/adsc.201801429
was diluted with ethyl acetate (30 mL), washed with 138.4, 137.3, 133.4, 129.9, 129.8, 129.4, 128.6, 128.3,
water (30 mL), extracted with ethyl acetate (3×30 127.1, 126.5, 124.1, 123.8, 117.8, 21.5, 21.4, 18.1.
mL), and dried over anhydrous Na
2
SO
4
and HRMS (EI): calcd for C20
H
18
2
O S: 322.1028; found,
concentrated in vacuo. The crude product was 322.1030.
purified by flash column chromatography on silica gel
to give the desired product 3w in 56% yield (4-(Methylthio)-5-(p-tolyl)furan-2-yl)(p-
(
1265.6mg).
tolyl)methanone (3d)
Following the general procedure to afford a yellow
1
solid in 74% yield, 59.6 mg. H NMR (400 MHz,
Preparation of α-iodo Acetophenone and
CDCl ): δ 7.99-7.92 (m, 3H), 7.32 (d, J = 6.6 Hz, 3H),
3
Sulfonium Salts
7
.27 (d, J = 8.0 Hz, 2H), 2.45 (s, 6H), 2.40 (s, 3H).
1
3
C NMR (100 MHz, CDCl ): δ 181.4, 154.12, 150.2,
3
Finely powdered CuO (0.8 g, 10.0 mmol) and I
2.53 g, 10.0 mmol) were added to a solution of
2
1
1
C
43.4, 139.2, 134.6, 129.5, 129.4, 129.2, 126.8, 126.5,
24.0, 117.2, 21.7, 21.5, 18.1. HRMS (EI): calcd for
(
acetophenone (1.2 g, 10.0 mmol) in anhydrous MeOH
20 mL). The mixture was refluxed for 1-2.5 h. After
20
H
18
O S: 322.1028; found, 322.1025.
2
(
disappearance of acetophenone (monitored by TLC),
the mixture was filtered and the solvent was removed
under reduced pressure. The residue was poured into
(
(
2-Methoxyphenyl)(5-(2-methoxyphenyl)-4-
methylthio)furan-2-yl)methanone (3e)
Following the general procedure to afford a yellow
1
0% Na
extracted with EtOAc (3 × 50 mL), and the organic
layer was dried (Na SO ). Removal of the solvent and
purification of the residue by column chromatography
2
S
2
O solution (50 mL), the mixture was
3
1
solid in 71% yield, 62.8 mg. H NMR (400 MHz,
CDCl ): δ 7.53 (d, J = 7.5 Hz, 1H), 7.47 (t, J = 8.9 Hz,
3
2
4
2
H), 7.39 (dd, J = 14.8, 6.8 Hz, 1H), 7.14 (s, 1H),
[22]
7.06-6.94 (m, 4H), 3.86 (s, 3H), 3.83 (s, 3H), 2.32 (s,
gave the desired product A in 90% yield.
1
3
3
1
1
5
3
H). C NMR (100 MHz, CDCl ): δ 182.3, 157.5,
3
Dimethyl sulfide (10 mmol) was added to a
solution of 2-bromoacetophenone (10 mmol) in
acetone (15 mL). After the mixture had been stirred
for 12 h, the residue was filtered and washed with
acetone. The solid product was used as sulfonium
bromide without further purification.[23]
57.2, 153.4, 151.6, 132.2, 131.2, 130.7, 129.69,
27.8, 123.1, 120.4, 120.2, 120.2, 118.4, 111.6, 111.3,
5.8, 55.5, 17.8. HRMS (EI): calcd for C20
54.0926; found, 354.0921.
H
18
4
O S:
(
(
4-Methoxyphenyl)(5-(4-methoxyphenyl)-4-
methylthio)furan-2-yl)methanone (3f)
(
4-(Methylthio)-5-phenylfuran-2-
Following the general procedure to afford a yellow
yl)(phenyl)methanone (3a)
1
solid in 73% yield, 64.6 mg. H NMR (400 MHz,
Prepared according to the general procedure to afford
1
CDCl
3
) H NMR (400 MHz, CDCl
3
) δ 8.07 (d, J = 8.0
1
a yellow solid in 83% yield, 61.0 mg. H NMR (400
Hz, 2H), 8.03 (d, J = 8.1 Hz, 2H), 7.95 (d, J = 8.0 Hz,
MHz, CDCl
3
) δ 8.05 (dd, J = 13.7, 7.6 Hz, 4H), 7.61
2
3
H), 7.33 (s, 1H), 7.04-6.97 (m, 4H), 3.91 (s, 3H),
(
d, J = 6.8 Hz, 1H), 7.53 (t, J = 7.1 Hz, 2H), 7.48 (t, J
1
3
.88 (s, 3H), 2.45(s, 3H). C NMR (100 MHz,
) δ 180.3, 163.3, 160.2, 154.0, 150.2, 132.4,
31.7, 129.9, 128.1, 124.1, 114.3, 114.1, 113.8, 55.6,
=
7.1 Hz, 2H), 7.43 – 7.37 (m, 1H), 7.35 (s, 1H), 2.48
13
CDCl
3
(
s, 3H). C NMR (101 MHz, CDCl
3
): δ 181.8, 153.8,
50.3, 137.2, 132.6, 129.5, 129.3, 129.1, 128.7, 128.5,
26.5, 124.1, 118.1, 18.1. HRMS (EI): calcd for
S: 294.0715; found: 294.0718.
1
5
3
1
1
C
5.4, 18.3. HRMS (EI): calcd for C20
54.0926; found, 354.0928.
H
18
4
O S:
18 14
H O
2
(
4-(Methylthio)-5-(4-(methylthio)phenyl)furan-2-
(
4-(Methylthio)-5-(o-tolyl)furan-2-yl)(o-
yl)(4-(methylthio)phenyl)methanone (3g)
tolyl)methanone (3b)
Following the general procedure to afford a yellow
Following the general procedure to afford a yellow
1
solid in 63% yield, 60.8 mg. H NMR (400 MHz,
1
solid in 73% yield, 58.8 mg. H NMR (400 MHz,
CDCl ): δ 7.98 (d, J = 8.2 Hz, 4H), 7.33 (t, J = 6.4 Hz,
3
CDCl ): δ 7.53 (d, J = 7.5 Hz, 2H), 7.40 (t, J = 7.4 Hz,
3
4
3
1
1
H), 7.31 (s, 1H), 2.56 (s, 3H), 2.53 (s, 3H), 2.47 (s,
1
2
H), 7.37-7.28 (m, 5H), 7.15 (s, 1H), 2.43 (s, 3H),
.40 (s, 3H), 2.32 (s, 3H). 13C NMR (100 MHz,
): δ 184.5, 156.8, 151.4, 137.8, 137.3, 137.2,
31.2, 130.9, 130.7, 130.2, 129.8, 128.4, 128.3, 125.5,
25.1, 123.7, 119.1, 20.7, 19.8, 18.1. HRMS (EI):
S: 322.1028; found, 322.1023.
1
3
H). C NMR (100 MHz, CDCl ): δ 180.5, 153.4,
3
50.2, 145.5, 140.3, 133.3, 129.8, 126.7, 126.0, 125.9,
25.0, 123.9, 117.6, 18.1, 15.2, 14.8. HRMS (EI):
CDCl
1
1
3
calcd for C20
H O S
18 2 3
: 386.0469; found, 386.0473.
calcd for C20
H
18
O
2
(
(
4-(tert-Butyl)phenyl)(5-(4-(tert-butyl)phenyl)-4-
methylthio)furan-2-yl)methanone (3h)
(
4-(Methylthio)-5-(m-tolyl)furan-2-yl)(m-
Following the general procedure to afford a yellow
tolyl)methanone (3c)
1
solid in 59% yield, 59.9 mg. H NMR (400 MHz,
CDCl ): δ 8.01 (d, J = 7.8 Hz, 4H), 7.52 (dd, J = 14.9,
Following the general procedure to afford a yellow
1
3
solid in 79% yield, 63.6 mg. H NMR (400 MHz,
7
1
1
1
.6 Hz, 4H), 7.36 (s, 1H), 2.47 (s, 3H), 1.38 (s, 9H),
CDCl ): δ 7.88 (d, J = 8.9 Hz, 2H), 7.82 (s, 2H), 7.43
3
1
3
.36 (s, 9H). C NMR (100 MHz, CDCl ): δ 181.3,
3
(
s, 2H), 7.36 (t, J = 7.7 Hz, 1H), 7.32 (s, 1H), 7.21 (d,
56.3, 154.0, 152.3, 150.4, 134.5, 129.4, 126.8, 126.3,
25.6, 125.4, 124.0, 117.3, 35.1, 34.8, 31.2, 31.1, 18.2.
1
3
J = 7.1 Hz, 1H), 2.46 (s, 6H), 2.43 (s, 3H). C NMR
100 MHz, CDCl ): δ 182.0, 154.0, 150.1, 138.4,
(
3
5
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Advanced Synthesis & Catalysis
10.1002/adsc.201801429
1
3
HRMS (EI): calcd for C26
H
30
O
2
S: 406.1967; found, 3H), 7.41-7.33 (m, 3H), 7.23 (s, 1H), 2.35 (s, 3H). C
NMR (100 MHz, CDCl ): δ 181.6, 154.0, 151.2,
37.1, 133.9, 131.9, 131.8, 131.7, 131.3, 131.1, 130.3,
130.3, 129.4, 128.0, 126.5, 123.4, 121.1, 18.0. HRMS
406.1969.
3
1
(
(
(
4-(Methylthio)-5-(2-
trifluoromethyl)phenyl)furan-2-yl)(2-
trifluoromethyl)phenyl)methanone (3i)
(EI): calcd for C18
361.9931.
H
12Cl
2
O S: 361.9935; found,
2
Following the general procedure to afford a yellow
1
solid in 52% yield, 55.9 mg. H NMR (400 MHz, (3-Chlorophenyl)(5-(3-chlorophenyl)-4-
CDCl3): δ 7.79-7.74 (m, 2H), 7.67-7.60 (m, 4H), 7.57
(
methylthio)furan-2-yl)methanone (3n)
1
3
Following the general procedure to afford a yellow
solid in 81% yield, 73.9 mg. H NMR (400 MHz,
(
t, J = 6.4 Hz, 2H), 7.30 (s, 1H), 2.33 (s, 3H).
C
1
NMR (100 MHz, CDCl3): δ 182.4, 153.6, 151.3,
1
1
36.4, 132.2, 131.5, 131.3, 130.3, 130.0, 129.6, 129.3, CDCl ) δ 8.02 (d, J = 17.7 Hz, 2H), 7.91 (dd, J = 13.3,
3
28.4, 127.0 (q, J = 5.1 Hz), 126.7 (dd, J = 9.5, 4.7 7.7 Hz, 2H), 7.59 (d, J = 8.0 Hz, 1H), 7.48 (t, J = 7.7
Hz), 124.9, 124.7, 122.7, 122.1, 120.8, 18.0. HRMS Hz, 1H), 7.40 (dd, J = 15.7, 7.9 Hz, 2H), 7.35 (s, 1H),
1
3
2
1
1
.49 (s, 3H). C NMR (100 MHz, CDCl ): δ 180.1,
3
(EI): calcd for C20
430.0459.
H
12
F
6
O S: 430.0462; found,
2
52.1, 150.1, 138.5, 134.8, 134.8, 132.7, 130.9, 130.0,
29.9, 129.4, 129.1, 127.4, 126.3, 124.5, 124.0, 119.6,
(
(
(
4-(Methylthio)-5-(4-
trifluoromethyl)phenyl)furan-2-yl)(4-
trifluoromethyl)phenyl)methanone (3j)
17.9. HRMS (EI): calcd for C18
H12Cl
2
O S: 361.9935;
2
found, 361.9936.
(
4-Chlorophenyl)(5-(4-chlorophenyl)-4-
Following the general procedure to afford a yellow
1
(methylthio)furan-2-yl)methanone (3o)
solid in 78% yield, 83.9 mg. H NMR (400 MHz,
CDCl
Following the general procedure to afford a yellow
3
): δ 8.14 (t, J = 9.4 Hz, 4H), 7.82 (d, J = 7.9 Hz,
1
solid in 81% yield, 73.9 mg. H NMR (400 MHz,
2
1
1
H), 7.74 (d, J = 8.0 Hz, 2H), 7.39 (s, 1H), 2.52 (s,
1
3
CDCl ) δ 7.99 (t, J = 6.3 Hz, 4H), 7.52 (d, J = 7.6 Hz,
3
H). C NMR (101 MHz, CDCl
3
) δ 180.5, 151.9,
2
3
1
1
H), 7.45 (d, J = 8.2 Hz, 2H), 7.35 (s, 1H), 2.48 (s,
50.4, 139.8, 134.2 (d, J = 32.8 Hz), 132.4, 130.6 (d,
1
3
H). C NMR (100 MHz, CDCl ): δ 180.3, 152.6,
3
J = 32.8 Hz), 129.6, 126.5, 125.7 (q, J = 3.8 Hz),
50.2, 139.2, 135.3, 135.1, 130.7, 129.0, 128.9, 127.8,
27.6, 123.9, 118.8, 18.0. HRMS (EI): calcd for
1
1
25.6 (q, J = 3.8 Hz), 125.1 (d, J = 24.5 Hz), 123.8,
22.3 (d, J = 25.1 Hz), 120.8, 17.8. HRMS (EI):
C
18
H
12Cl
2
O S: 361.9935; found, 361.9938.
2
calcd for C20
H
12
F
6
O S: 430.0462; found, 430.0465.
2
(
(
2-Bromophenyl)(5-(2-bromophenyl)-4-
methylthio)furan-2-yl)methanone (3p)
(
4-(Methylthio)-5-(2-nitrophenyl)furan-2-yl)(2-
nitrophenyl)methanone (3k)
Following the general procedure to afford a yellow
Following the general procedure to afford a yellow
1
1
solid in 63% yield, 71.2 mg. H NMR (400 MHz,
CDCl ): δ 7.67 (t, J = 7.7 Hz, 2H), 7.52 (d, J = 7.3 Hz,
solid in 65% yield, 62.4 mg. H NMR (400 MHz,
3
CDCl ): δ 8.21 (d, J = 8.2 Hz, 1H), 7.92 (d, J = 8.1
3
2
1
H), 7.36 (ddd, J = 26.3, 15.5, 7.6 Hz, 4H), 7.22 (s,
Hz, 1H), 7.82 (t, J = 7.5 Hz, 1H), 7.72 (dd, J = 21.5,
1
3
H), 2.34 (s, 3H). C NMR (100 MHz, CDCl ): δ
3
7
1
1
1
1
3
.4 Hz, 3H), 7.59 (dd, J = 15.5, 7.6 Hz, 2H), 7.40 (s,
H), 2.41 (s, 3H). 1 C NMR (100 MHz, CDCl
3
182.4, 155.4, 150.8, 139.1, 133.4, 133.4, 132.3, 131.7,
3
): δ
1
1
4
31.3, 130.1, 129.4, 127.1, 127.1, 123.6, 123.4, 120.9,
20.0, 18.1. HRMS (EI): calcd for C18
49.8925; found, 449.8922.
80.5, 151.2, 150.6, 148.1, 146.8, 134.2, 133.9, 132.7,
31.4, 131.2, 130.4, 129.2, 124.7, 124.4, 123.0, 121.6,
H12Br
2
2
O S:
21.4, 17.9. HRMS (EI): calcd for C18
84.0416; found, 384.0420.
H
12
N
2
O S:
6
(
(
3-Bromophenyl)(5-(3-bromophenyl)-4-
methylthio)furan-2-yl)methanone (3q)
(
4-(Methylthio)-5-(3-nitrophenyl)furan-2-yl)(3-
Following the general procedure to afford a yellow
nitrophenyl)methanone (3l)
1
solid in 85% yield, 96.1 mg. H NMR (400 MHz,
CDCl ): δ 8.19 (s, 1H), 8.17 (s, 1H), 7.96 (dd, J =
1
=
Following the general procedure to afford a yellow
1
3
solid in 89% yield, 85.4 mg. H NMR (400 MHz,
5.7, 7.8 Hz, 2H), 7.74 (d, J = 7.9 Hz, 1H), 7.52 (t, J
CDCl ) δ 8.97 (d, J = 18.8 Hz, 2H), 8.51 (d, J = 8.2
3
9.6 Hz, 1H), 7.41 (t, J = 7.9 Hz, 1H), 7.38-7.30 (m,
Hz, 1H), 8.38 (dd, J = 13.2, 7.8 Hz, 2H), 8.25 (d, J =
.2 Hz, 1H), 7.78 (t, J = 8.0 Hz, 1H), 7.69 (t, J = 8.0
13
2
H), 2.49 (s, 3H). C NMR (100 MHz, CDCl
3
): δ
8
13
179.9, 152.0, 150.1, 138.7, 135.6, 132.3, 132.0, 131.1,
Hz, 1H), 7.49 (s, 1H), 2.57 (s, 3H). C NMR (100
MHz, CDCl ): δ 178.7, 151.0, 150.4, 148.6, 148.2,
37.8, 134.9, 131.6, 130.6, 130.0, 130.0, 127.3, 124.4,
23.8, 123.5, 121.4, 121.1, 17.8. HRMS (EI): calcd
S: 384.0416; found, 384.0421.
1
1
4
30.2, 130.1, 129.1, 127.8, 124.9, 123.9, 122.9, 122.8,
19.6, 17.9. HRMS (EI): calcd for C18
49.8925; found, 449.8929.
3
H12Br
2
2
O S:
1
1
for C18
H N O
12 2 6
(
(
4-Bromophenyl)(5-(4-bromophenyl)-4-
methylthio)furan-2-yl)methanone (3r)
(
(
2-Chlorophenyl)(5-(2-chlorophenyl)-4-
methylthio)furan-2-yl)methanone (3m)
Following the general procedure to afford a yellow
1
solid in 81% yield, 85.7 mg. H NMR (400 MHz,
CDCl ): δ 7.90 (t, J = 8.4 Hz, 4H), 7.68 (d, J = 7.7 Hz,
Following the general procedure to afford a yellow
1
3
solid in 67% yield, 61.1 mg. H NMR (400 MHz,
CDCl ) δ 7.55 (t, J = 8.4 Hz, 2H), 7.47 (t, J = 10.1 Hz,
2
1
H), 7.60 (d, J = 7.9 Hz, 2H), 7.34 (s, 1H), 2.48 (s,
3
1
3
H). C NMR (100 MHz, CDCl
3
): δ 180.5, 152.7,
6
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Advanced Synthesis & Catalysis
10.1002/adsc.201801429
1
1
C
50.2, 135.7, 132.0, 131.8, 130.8, 128.2, 127.8, 123.9, Following the general procedure to afford a pale
1
23.4, 119.0, 18.0. HRMS (EI): calcd for yellow solid in 59% yield, 60.8 mg. H NMR (400
S: 449.8925; found, 449.8924.
MHz, CDCl ): δ 8.04 (d, J = 6.3 Hz, 2H), 7.48 (d, J =
.5 Hz, 1H), 7.35 (d, J = 8.5 Hz, 1H), 2.46 (s, 3H),
4-(Methylthio)-5-(naphthalen-2-yl)furan-2-
18
H12Br
O
2 2
3
8
2
(
.40 (s, 3H). 13C NMR (100 MHz, CDCl ): δ 175.74 ,
154.59 , 154.06 , 135.53 , 135.08 , 125.35 , 122.89 ,
3
yl)(naphthalen-2-yl)methanone (3s)
Following the general procedure to afford a yellow 121.48 , 117.85 , 20.97 , 16.41. HRMS (EI): calcd for
1
solid in 73% yield, 71.9 mg. H NMR (400 MHz,
CDCl ): δ 8.63 (s, 1H), 8.57 (s, 1H), 8.21 (d, J = 8.7
Hz, 1H), 8.08 (t, J = 10.1 Hz, 1H), 8.00 (dd, J = 12.6, (4-(Methylthio)-5-phenylfuran-2-
C
11
H
10
2
O S: 206.0402; found, 206.0406.
3
8
7
7
.3 Hz, 2H), 7.96-7.89 (m, 3H), 7.87-7.81 (m, 1H), yl)(phenyl)methanone (3a-d
4
)
.69-7.55 (m, 2H), 7.52 (dd, J = 5.8, 3.1 Hz, 2H), Following the general procedure to afford a yellow
.44 (s, 1H), 2.51 (s, 4H). 13C NMR (10O MHz, solid in 81% yield. H NMR (400 MHz, CDCl
) δ
1
3
CDCl ): δ 181.6, 153.8, 150.6, 135.4, 134.5, 133.2, 8.04 (dd, J = 14.2, 7.7 Hz, 4H), 7.62 (t, J = 7.1 Hz,
3
1
1
1
3
33.1, 132.5, 130.9, 129.5, 128.7, 128.5, 128.4, 127.8, 1H), 7.53 (t, J = 7.2 Hz, 2H), 7.47 (t, J = 7.3 Hz, 2H),
27.7, 127.0, 126.9, 126.9, 126.7, 126.4, 125.2, 124.2, 7.42-7.36 (m, 1H).]
23.5, 118.6, 18.1. HRMS (EI): calcd for C26
H
18
O S:
2
94.1028; found, 394.1023.
Acknowledgements
Thiophen-2-yl(5-(thiophen-2-yl)furan-2-
yl)methanone (3t)
Financial support from the National Science Foundations of
China (No. 21572049) are gratefully acknowledged.
Following the general procedure to afford a yellow
1
solid in 85% yield, 60.0 mg. H NMR (400 MHz,
CDCl ): δ 8.19 (d, J = 3.0 Hz, 1H), 7.75 (d, J = 4.5
3
References
Hz, 2H), 7.46 (d, J = 5.9 Hz, 1H), 7.38 (d, J = 3.1 Hz,
H), 7.31-7.27 (m, 1H), 7.24 (t, J = 3.9 Hz, 1H), 2.48
1
1
3
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49.6, 141.6, 137.6, 137.0, 134.3, 134.2, 133.9, 128.3,
27.8, 122.7, 117.6, 18.2. HRMS (EI): calcd for
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1
1
C
H
14 10
O
2 3
S
3
-(Methylthio)-4H-chromen-4-one (3v)
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1
solid in 56% yield, 53.8 mg. H NMR (400 MHz,
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3
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H
8
O
2
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1
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solid in 63% yield, 71.2 mg. H NMR (400 MHz,
CDCl ): δ 8.18 (d, J = 8.5 Hz, 1H), 7.99 (s, 1H), 7.47
3
1
3
(
s, 1H), 7.39 (d, J = 8.6 Hz, 1H), 2.41 (s, 3H).
NMR (100 MHz, CDCl ): δ 174.8, 156.3, 153.3,
39.9, 127.5, 126.3, 122.6, 121.6, 118.1, 16.0. HRMS
EI): calcd for C10 ClO S: 225.9855; found,
C
3
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8
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2
013, 15, 13, 3206-3209.
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8
0, 5364-5368.
3
1
34.0, 131.4, 125.4, 124.0, 122.2, 119.8, 16.1. HRMS [8] S. Manna, A. P. Antonchick, Org. Lett. 2015, 17,
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EI): calcd for C10
H
7
ClO
2
S: 225.9855; found,
4300-4303.
225.9857.
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Advanced Synthesis & Catalysis
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10.1002/adsc.201801429
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Direct Assembly of Polysubstituted Furans via
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