One-pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water

Article abstract of DOI:10.1016/j.tet.2020.131635

A novel, facile and efficient strategy for the one-pot synthesis of β-ketosulfones from readily available sulfonyl chloride, hydrazine hydrate and vinyl azides is described. The reaction proceeded very smoothly affording diverse β-ketosulfones in moderate to good yields. This new procedure has the advantages of environmental benign, easy and simple operation, low cost and wide tolerance of functional groups, which provides a highly fascinating protocol to access β-ketosulfones.

Full text of DOI:10.1016/j.tet.2020.131635

Journal Pre-proof
One-pot Synthesis of β-Ketosulfones from Sulfonyl Chloride, Hydrazine Hydrate and
Vinyl Azide in Water
Yaohong Zhang, Mengqiang Luo, Yan Li, Runfu Shen, Chenze Qi, Hai Wang, Kai
Cheng
PII:
S0040-4020(20)30842-5
https://doi.org/10.1016/j.tet.2020.131635
TET 131635
DOI:
Reference:
To appear in: Tetrahedron
Received Date: 7 August 2020
Revised Date: 18 September 2020
Accepted Date: 27 September 2020
Please cite this article as: Zhang Y, Luo M, Li Y, Shen R, Qi C, Wang H, Cheng K, One-pot Synthesis
of β-Ketosulfones from Sulfonyl Chloride, Hydrazine Hydrate and Vinyl Azide in Water, Tetrahedron,
https://doi.org/10.1016/j.tet.2020.131635.
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One-pot Synthesis of β-Ketosulfones from Sulfonyl
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Chloride, Hydrazine Hydrate and Vinyl Azide in Water
† Hai Wang†
Mengqiang Luo,a b ,Yaohong Zhang, *a Yan Li,a Runfu Shen,a Chenze Qi a and Kai Cheng*a
aSchool of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine
Chemicals Process, Shaoxing University, Shaoxing,312000, Zhejiang, P. R. China and
bSchool of life science, Shaoxing University, Shaoxing, 312000, Zhejiang, P. R. China
N3
O
O
S
O
S
O
S
O
1
R1
Et3N, H2O
0 o
R2
2
NH2NH2.H2O
R1
NHNH2
R1
Cl
R2
CuSO4.5H2O (10 mol%)
H2O, 80 oC, 4h
O
C
O
3

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One-pot Synthesis of β-Ketosulfones from Sulfonyl
Leave this area blank for abstract info.
Chloride, Hydrazine Hydrate and Vinyl Azide in Water
† †
Yaohong Zhang,a Mengqiang Luo,a Yan Li,a Runfu Shen,a Chenze Qi,a Hai Wang*b and Kai Cheng*a
aSchool of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine
b
Chemicals Process, Shaoxing University, Shaoxing,312000, Zhejiang, P. R. China and School of life science,
Shaoxing University, Shaoxing, 312000, Zhejiang, P. R. China

1
Tetrahedron
journal homepage: www.elsevier.com
One-pot Synthesis of β-Ketosulfones from Sulfonyl Chloride, Hydrazine Hydrate and Vinyl Azide in
Water
† †
Yaohong Zhang,a Mengqiang Luo,a Yan Li,a Runfu Shen,a Chenze Qi,a Hai Wang*b and Kai Cheng*a
aSchool of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University,
Shaoxing,312000, Zhejiang, P. R. China and bSchool of life science, Shaoxing University, Shaoxing, 312000, Zhejiang, P. R. ChinaCollege of Pharmaceutical
Sciences, Zhejiang University, Hangzhou 310058, P. R. China.
*Corresponding author
† Contributed equally to this work
ARTICLE INFO
ABSTRACT
A novel, facile and efficient strategy for the one-pot synthesis of β-ketosulfones from readily available
sulfonyl chloride, hydrazine hydrate and vinyl azides is described. The reaction proceeded very
smoothly affording diverse β-ketosulfones in moderate to good yields. This new procedure has the
advantages of environmental benign, easy and simple operation, low cost and wide tolerance of
functional groups, which provides a highly fascinating protocol to access β-ketosulfones.
Article history:
Received
Received in revised form
Accepted
Available online
Keywords:
one-pot synthesis
β-ketosulfones
vinyl azides
2012 Elsevier Ltd. All rights reserved.
sulfonyl chloride
hydrazine hydrate
1. Introduction
first copper-catalyzed oxysulfonylation of alkenes with dioxygen
and sulfonylhydrazides leading to β-ketosulfones (Scheme 1a).
β-Ketosulfone, as an important kind of organic sulfones, is
In 2016, CF3COOH-catalyzed oxysulfonylation of alkenes was
discovered using dioxygen as the oxidant and sulfonylhydrazides
as the sulfone source (Scheme 1b)[12]. In 2017, tetra-n-
butylammonium bromide-mediated aerobic oxidative synthesis
of β-ketosulfones was achieved from styrenes and
sulfonylhydrazides in the presence of TBHP/O2 with a high atom
[1]
frequently found in naturally active products
and synthetic
pharmaceuticals [2], and it displays a wide range of biologically
and pharmaceutically activities including anticancer, anti-
infectious, antifungal, antiviral activities, as well as non-
cytotoxic urease and 11β-HSD1 inhibiton[3]. In addition, it is also
valuable and highly desirable synthons in constructing
pharmacologically active compounds and various important
organic compounds such as lycopodine alkaloidsand, halaven,
various sulfones, dihydropyrans, tetrahydrofurans, chromans,
pyrroles, pyrazole, thiadiazole and so on [4]. Thus, it is more
highly demanded for the development of new synthetic procedure
of β-ketosulfone and its derivatives.
economy[8b]
.
Later, Yu’s group[8c] presented the oxaditive
sulfonylation of vinyl azide with sulfonylhydrazides to access β-
ketosulfone in the presnce of KI/TBHP, but corrosive HOAc was
used as the solvent (Scheme 1c). In addition, other alternative
methods for the syntheis of β-keto sulfones have also been
disclosed applying sulfonylhydrazides as the sulfone source, such
as visible-light-promoted oxidative difunctionalization of
terminal alkynes using Ru(bpy)3Cl2 as photocatalyst and
dioxygen as the oxidant with NaOAc/KI as the necesssary
additives, and oxysulfonylation of alkenes applying
methyleneblue as photocatalyst under air atmosphere with
DABCO as the essential base[14], together with the photo-
mediated decarboxylative ketonization of atropic acids
employing fluorescein as a photocatalyst and NaHCO3/KI as
the essential additive with dioxygen as a natural oxygen
source[15]. However, to the best of our knowledge, there is no
example presenting the one-pot synthesis of β-ketosulfones from
sulfonyl chloride, hydrazine hydrate and vinyl azide using eco-
Considerable efforts have been devoted towards the
synthesis of β-ketosulfone on account of its wide range of
biological activities and chemical utilization to serve as important
building fragment in organic synthesis. Various functionalized
sulfonyl precursors including sulfinic acids[5], sodium sulfinate[6],
sulfonyl chlorides[7], sulfonylhydrazides[8], thiophenols[9],
dimethyl sulfoxide[10] and sulfur dioxide[11]were generally
employed to construct β-ketosulfones. Among them,
sulfonylhydrazides, as a sulfonylating source, have attracted
more attention of chemists and have been applied for the
synthesis of β-ketosulfones from alkenes or alkynes owing to its
advantage of low cost, good stability and readily availability. In
2013, Wang and coworkers[8a]reported an elegant work for the
.
friendly water as the solvent and CuSO4 5H2O as the catalyst to
access β-ketosulfones.

2
Tetrahedron
o
1) Previous work：
9-13). When the reaction was performed at 80 C, the target
product 3b could be obtained in 88% yield(Table 1, entry 16),
which was higher than that of 60 oC and 100 oC.
Table 1 Optimization of reaction conditionsa.
Entry
Catalyst
Solvent
T (0C)
t (h)
Yield(%) b
1
2
PdCl2
CuCl2
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
THF
60
60
60
60
60
60
60
60
60
60
60
60
60
80
100
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
49
76
31
57
80
40
38
trace
55
43
42
53
81
88
86
2) This work：
3
ZnCl2
4
NiSO4.6H2O
CuSO4.5H2O
MnSO4
5
6
Scheme 1. Strategies for construction of β-ketosulfones from alkenyls and
7
FeSO4
___
sulfonylhydrazides
8
Vinyl azide, as an attractive and challenging synthon, has
attracted much attention in the construction of structurally
diverse molecules skeletons[16]. In addition, vinyl azides, serving
as a radical acceptor [17], can be added easily to other newly
generated radicals, subsequently the characteristic properties of
the azide group promotes azide group to generate corresponding
iminyl radicals, which allows the formation of some useful
building fragment[18]. Herein, based on the potential chemical
reactivity of vinyl azide and sulfonyl hydrazine, we report the
one-pot synthesis of β-ketosulfones from sulfonyl chloride,
hydrazine hydrate and vinyl azide.
9
CuSO4.5H2O
CuSO4.5H2O
CuSO4.5H2O
CuSO4.5H2O CH3CN
CuSO4.5H2O
10
11
12
13
14
15
DMSO
DMF
H2O
H2O
H2O
.
CuSO4 5H2O
CuSO4.5H2O
a.The reaction conditions: vinyl azide (1.0 mmol), 4-toluenesulfonyl
chloride(1.0 mmol), hydrazine hydrate (80%) (1.2 mmol), Et3N (1.2 mmol),
catalyst(10% mmol), 10 mL of solvent.
2. Results and discussion
b.Isolated yield; The most efficient entry is highlighted in bold.
The structures of the β-Ketosulfones were characterized by 1H NMR, 13C NMR and HRMS.
To establish the optimal reaction conditions, the reaction of
4-methylbenzene sulfonyl chloride, hydrazine hydrate and α-
phenylvinyl azide was chosen as the model reaction. Initially, we
explored the formation of 4-methylbenzenesulfono hydrazide
according to the reported procedures[19], hydrazine hydrate(1.2
equiv.) was added dropwise to a solution of the sulfonyl chloride
(1.0 equiv) in water 0 oC. Then Et3N(1.2 equiv.) was added
dropwise to the reaction system and the resulting solution was
stirred at 0 oC until the complete consumption of sulfonyl
chloride. Subsequently, vinyl azides (1.0 equiv) and metal salt
(10 mol%) were added to the reaction system to test the effect of
catalyst on the oxysulfonylation reaction between α-phenylvinyl
azide and 4-methylbenzenesulfonohydrazide to access β-
Under the established optimal conditions, the scope and
limitations of the reaction were tested and some results are shown
in Table 2. Firstly, various sulfonohydrazides prepared from
sulfonyl chlorides and hydrazine hydrate were used to test the
scope of the reaction. Arenesulfony chlorides bearing both
electron-donating groups (R = 4-Methyl, 4-Methoxy, 2-Methyl,
2, 4, 6-tri-Methyl-) and electronwithdrawing groups (R = 4-F, 4-
Cl) could be efficiently formed into the corresponding β-
ketosulfones in moderate to good yields (Table 2, 3b-3g).
Heteroaromatic and condensed aromatic sulfonyl chlorides were
also tolerated to furnish the corresponding products in good
yields (Table 2, 3h–3j). Furthermore, substituents at different
positions and with different numbers on the arene ring of sulfonyl
chlorides do not significantly affect the efficiency of the reaction
(Table 2, 3b, 3d and 3e). With respect to aliphatic sulfonyl
chlorides, methanesulfonyl chloride and propanesulfonyl chloride
were also able to afford the expected products with the lower
yields ( 75% and 71%) due to the low efficiency in the formation
of sulfonyl hydrazine (Table 2, 3k and 3l). In addition, the scope
of the vinyl azides was also investigated and the results showed
that the reactions of vinyl azides containing electron-donating or
electron-withdrawing substituents on the aryl ring proceeded
smoothly and efficiently, and leading to the desired products with
the yields between 82% and 89% (Table 2, 3m-3t). Functional
groups such as 4-F, 4-Cl 4-Br, 4-Methyl and 4-Methoxy were
compatible with this reaction providing the corresponding
products 3m-3q, which could be applied in further
o
ketosulfone at 60 C. The result showed that the reaction was
very sluggish in the absence of ZnCl2, MnSO4 nad FeSO4 in
EtOH (Table 1, entries 3, 6 and 7). PdCl2 and NiSO4.6H2O were
also applied to test the effect on the reaction, the results indicated
that the product 3b was achieved in the yields of 49% and 57%,
respectively (Table 1, entries 1 and 4). Furthermore, copper(II)
.
salts such as CuCl2 and CuSO4 5H2O were examined to increase
.
the reaction yield (Table 1, entries 2 and 5), and CuSO4 5H2O
was found to be the most effective catalyst to give the
corresponding product 3b in 80% yield (Table 1, entry 5). When
no catalyst was added in the reaction, only trace product was
generated (Table 1, entry 8). A range of protic solvents and
aprotic solvents were then screened, and the results demonstrated
that protic solvents was beneficial to the reaction and water was
proven to be the optimal reaction medium (Table 1, entries 4 and

3
transformations. As shown in Table 2, the generation of 3u-3w
indicated again that different types of substituents on the aryl ring
of vinyl azides have no significant effect on the reaction
efficiency (Table 2,). α-Phenylvinyl azides bearing methoxy at 4-,
3- and 2- position of the aromatic ring were also tolerated to
afford the corresponding product 3q, 3r, 3s in the yield of 85%,
87% and 84%, respectively. Heterocycle-based vinyl azides
also provided the desired β-ketosulfone 3t in 82% yield.
reaction involves radical species [Eq.(2)].When the reaction
was carried out in aprotic solvent(DMSO) or N2 atmosphere, 3b
was obtained only in 43% and 31% yield respectively, the result
demonstrated that H+ and O2 is necessary for the transformation
[Eq.(3-4)]. Further control experiments showed that no
corresponding β-keto sulfone 3b was obtained when the reaction
.
was performed in the absence of CuSO4 5H2O, which implied
.
that CuSO4 5H2O may serve as radical species initiator [Eq.(5)].
O
S
O
S
NH2NH2.H2O
H3C
Cl
TsNHNH2
H3C
NHNH2
Table 2 Scope of the reaction of vinyl azides, sulfonyl chlorides
0 oC, Et3N,H2O
Eq.(1)
O
O
and hydrazine hydrate under optimal conditionsa.
1
1
N3
Ph
O
S
O
O
NH2NH2.H2O
2
H3C
S
Cl
O
TsNHNH2
0 oC, Et3N,H2O
Eq.(2)
CuSO4.5H2O(10mol%) H3C
TEMPO(5.0 equiv.),
H2O, 80 oC, air, 4h
O
3b, 0%
O
S
O
O
S
O
O
S
O
N3
O
S
O
O
O
O
NH2NH2.H2O
2
Ph
O
H3C
H3C
S
Cl
Cl
H3CO
TsNHNH2
TsNHNH2
O
CuSO4.5H2O(10mol%)
DMSO, 80 oC, air, 4h
3b, 86%
0 oC,Et3N,DMSO
3c, 86%
O
Eq.(3)
Eq.(4)
1
1
H3C
3a, 88%
3b, 43%
O
S
O
CH3
O
O
O
S
O
N3
CH3
O
S
O
S
O
S
NH2NH2.H2O
O
2
O
Ph
O
O
H3C
0 oC, Et3N,H2O
Cl
H3C
CH3
CuSO4.5H2O(10mol%)
H2O, 80 oC, N2, 4h
H3C
O
3b, 31%
3f, 87%
3d, 81%
3e, 83%
O
S
O
O
S
O
O
S
O
O
S
O
N3
O
S
O
NH2NH2.H2O
2
O
O
Ph
O
N
H3C
Cl
Eq.(5)
TsNHNH2
0 oC, Et3N,H2O
3b, 0%
F
H3C
3g, 80%
O
H2O, 80 oC, air, 4h
3i, 84%
1
3h, 84%
Scheme 2. Control experiments
O
S
O
O
O
O
O
S
S
H3C
O
O
On the basis of the results presented above and previous
O
S
3l, 71%
reports[8],we proposed a possible mechanism for the generation of
β-ketosulfones in Scheme 3. Initially, the nucleophilic
substitution of the sulfonyl chloride by hydrazine afford the
sulfonyl hydrazide in the assistance of Et3N. Subsequently, the
3j, 85%
3k, 75%
O
S
O
O
S
O
O
S
O
O
O
O
Br
Cl
F
3m, 83%
3o, 86%
3n, 89%
.
sulfonyl radical 7 and OOH species were generated from 4 and
O
S
O
O
S
O
O
S
O
O2 with the release of N2 via single electron transfer and the
deprotonation process. The transformations occurred faster when
high oxidation-value metal salts such as Cu (II) species were
employed. Afterwards, the radical addition of the resultant
sulfonyl radical 7 to vinyl azides 2 afforded the iminyl radical 8.
Subsequently, a single-electron transfer occured in the assistance
of H2O2 to produce intermediate 9, which undergoes hydrolysis
to achieve the β-ketosulfones 3.
OCH3
O
O
O
CH3
OCH3
3r, 87%
3p, 88%
3q, 85%
O
S
O
O
S
O
O
S
O
OCH3
S
O
O
O
H3C
Ph
3t, 82%
3s, 84%
3u, 88%
O
O
O
S
O
S
N3
O
O
NH
O
O
S
O
S
O
S
R1
H3C
Br
R2
R1
Hydrolysis
O
S
Et3N
NH3NH2
H3C
Cl
2
R1
NHNH2
4
R2
R1
Cl
R2
3w, 87%
O
3v, 85%
O
O
3
9
H2O
O
1
2CuII
2O2
a.The reaction conditions: 1a (1.0 mmol), 2a (1.0 mmol), hydrazine hydrate
(80%) (1.2 mmol), Et3N (1.2 mmol), CuSO4.5H2O (10% mmol), 5 mL of
H2O, 4 h unless otherwise noted.
O2
fast slow
2CuI
H2O
2H+
2HOO
HOO
b. Isolated yield
O2
O
S
O
6
N
O
S
O
S
O
S
R1
HOOH
R1
N N
R1
R1
N
NH
R2
O
2
O
CuII
CuI
The structures of the quinoxalines were characterized by 1H NMR, 13C NMR and HRMS.
5
N2
O
2H+
8
7
O2
Scheme 3. Proposed Mechanism
Several control experiments were conducted to investigate
the reaction mechanism (Scheme 2). Firstly, the formation of 4-
methylbenzenesulfono hydrazide was explored according to a
literature procedure[19], and producing the sulfonohydrazide in
almost 100% yield [Eq.(1)]. Subsequently, radical trapping
experiments were performed. As shown in Scheme 1, when 5.0
equiv. of TEMPO (2, 2, 6, 6-tetramethylpiperidinyloxyl, a well
known radical-capturing species) was used in the reaction under
standard conditions, no desired product 3b was detected,
suggesting that the reaction was completely inhibited and the
3. Conclusion
In summary, we have disclosed a facile, efficient and one-
pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine
hydrate and vinyl azide in water. Moreover, this procedure is
distinguished by easy operation, low cost catalyst, eco-friendly
solvent and broad substrate scope, which provides a highly
fascinating protocol to access β-ketosulfones.

4
Tetrahedron
4. Experimental section
4.1. General
Commercially available materials were used as received,
1-Phenyl-2-(o-tolylsulfonyl)ethan-1-one(3d)[6a] 1H NMR(400
:
MHz, CDCl3) δ 7.96 (d, J = 7.6 Hz, 2H), 7.89 (d, J = 7.6 Hz, 1H),
7.62 (t, J = 7.2 Hz, 1H), 7.53 – 7.46 (m, 3H), 7.36 – 7.33 (m, 2H),
4.76 (s, 2H), 2.73 (s, 3H). 13C NMR(100 MHz, CDCl3) δ 188.20,
138.60, 137.14, 136.05, 134.61, 134.49, 133.03, 130.82, 129.64,
129.10, 126.87, 63.17, 20.80. HRMS(ESI) M/Z calcd for
C15H15O3S. [M + H]+: 275.0736. Found: 275.0744.
unless otherwise noted. All solvents were purified according to
standard methods prior to use. Purifications of reaction products
were carried out by chromatography using silica gel (200-300
2-(Mesitylsulfonyl)-1-phenylethan-1-one(3e)[15] 1H NMR(400
:
mesh). H NMR and 13C NMR spectra were recorded on a 400
1
MHz spectrometer (1H: 400 MHz, 13C: 100 MHz), and data are
reported as follows: chemical shift, integration, multiplicity
(s=singlet, d=doublet, t=triplet, q=quartet, m=multiplet) and the
coupling constants J are given in Hz. Chemical shifts (δ) were
reported in ppm, DMSO-d6 (δ=2.50) or CDCl3 (δ=7.26) was used
MHz, DMSO) δ 7.99 – 7.96 (m, 2H), 7.70 – 7.66 (m, 1H), 7.54 –
7.50 (m, 2H), 7.05 (s, 2H), 5.13 (s, 2H), 2.52 (s, 6H), 2.27 (s, 3H).
13C NMR(100 MHz, DMSO) δ 189.23, 143.53, 139.69, 135.98,
134.24, 133.51, 132.07, 129.28, 128.79, 63.02, 22.39, 20.53.
HRMS(ESI) M/Z calcd for C17H19O3S. [M + H]+: 303.1049.
Found: 303.1058.
1
as internal standard for H NMR, DMSO-d6 (δ=39.5) or CDCl3
2-((4-Chlorophenyl)sulfonyl)-1-phenylethan-1-one(3f)[8a]
:
1H
(δ=77.26) was used as internal standard for 13C NMR. HRMS
data was obtained using Agilent Technologies 6224 TOF
LC/MS. Melting points were measured on a BÜCHI B-540
melting point apparatus and uncorrected. The starting material
vinyl azides 2 were synthesized according to the procedures in
NMR(400 MHz, DMSO) δ 7.93 (d, J = 8.0 Hz, 2H), 7.83 (d, J =
8.4 Hz, 2H), 7.66 – 7.63 (m, 1H), 7.54 – 7.48 (m, 4H), 4.74(s,
2H). 13C NMR(100 MHz, CDCl3) δ 188.12, 140.34, 137.32,
135.80, 134.82, 130.44, 129.80, 129.51, 129.21, 63.61. HRMS
(ESI) M/Z calcd for C14H12ClO3S. [M + H]+: 295.0190. Found:
295.0198.
the literature[20]
.
2-((4-Fluorophenyl)sulfonyl)-1-phenylethan-1-one(3g)[8a]
:
1H
General Procedure for the Synthesid of 3a
-3w
At 0 °C, hydrazine hydrate (Conc.80%)(1.2 mmol, 1.2 equiv) was
added dropwise to a solution of the sulfonyl chloride (1.0 mmol)
in 5mL water. Then Et3N (1.2 mmol, 1.2 equiv) was added
dropwise to the reaction system and the resulting solution was
stirred at 0 °C until the completion of sulfonyl chloride.
NMR(400 MHz, CDCl3) δ 7.94 – 7.90 (m, 4H), 7.64 (t, J = 7.6
Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.25 (t, J = 8.4 Hz, 2H), 4.75 (s,
2H). 13C NMR (100 MHz, CDCl3) δ 188.24, 166.36 (d, J = 256
Hz), 135.86, 134.73, 131.89(d, J = 10 Hz), 129.47, 129.16,
116.76(d, J = 22 Hz), 63.66. HRMS(ESI) M/Z calcd for
C14H12FO3S. [M + H]+: 279.0486. Found: 279.0489.
.
Subsequently, CuSO4 5H2O (25 mg, 10 mol%) and vinyl azides
(1.2 mmol, 1.2 equiv) were added to the reaction system. The
reaction mixture was heated and magnetically stirred at 80 °C for
4 h. Upon completion of the reaction, the resulting mixture was
diluted with saturated NaCl solution and extracted with
ethylacetate, the combined organic extracts were dried over
Na2SO4, concentrated and purified by chromatography
(petroleum ether/ethylacetate) on silica gel to provide the
corresponding products 3a-3w.
2-(Naphthalen-2-ylsulfonyl)-1-phenylethan-1-one(3h)[15]
:
1H
NMR(400 MHz, CDCl3) δ 8.46 (s, 1H), 8.01 – 7.92 (m, 5H), 7.87
(dd, J = 8.6, 1.7 Hz, 1H), 7.70 – 7.67 (m, 1H), 7.65 – 7.59 (m,
2H), 7.46 (t, J = 7.7 Hz, 2H), 4.82 (s, 2H). 13C NMR(100 MHz,
CDCl3) δ 188.25, 135.98, 135.84, 135.78, 134.62, 132.26, 130.92,
129.86, 129.80, 129.76, 129.55, 129.09, 128.26, 127.98, 123.20,
63.80. HRMS(ESI) M/Z calcd for C18H15O3S. [M + H]+:
311.0736. Found: 311.0742.
1-Phenyl-2-(quinolin-4-ylsulfonyl)ethan-1-one(3i): m.p. 112.4
~ 114.0 oC, 1H NMR(400 MHz, CDCl3) δ 9.1 (dd, J = 1.6, 4.0 Hz,
1H), 8.50 (dd, J = 1.6, 7.6 Hz, 1H), 8.29 (dd, J = 1.6, 8.4 Hz, 1H),
8.13 (dd, J = 1.6, 8.4 Hz, 1H), 7.97 – 7.94 (m, 2H), 7.69 (t, J =
7.6 Hz, 1H), 7.59 – 7.57 (m, 2H), 7.45 (t, J = 8.0 Hz, 2H), 5.52 (s,
2H). 13C NMR(100 MHz, CDCl3) δ 189.19, 151.74, 144.22,
137.14, 136.30, 136.18, 134.90, 134.34, 132.43, 129.25, 129.11,
128.97, 125.93, 122.55, 62.68. HRMS(ESI) M/Z calcd for
C17H14NO3S. [M + H]+: 312.0689. Found: 312.0681.
1-Phenyl-2-(phenylsulfonyl)ethan-1-one(3a)[8a] 1H NMR(400
:
MHz, DMSO) δ 7.96 – 7.94 (m, 2H), 7.92 – 7.89 (m, 2H), 7.73 (t,
J = 7.6 Hz, 1H), 7.64 (q, J = 7.6 Hz, 3H), 7.51 (t, J =8.0 Hz, 2H),
5.35 (s, 2H). 13C NMR(100 MHz, DMSO) δ 189.12, 139.51,
135.71, 134.26, 134.05, 129.26, 129.10, 128.80, 128.06, 62.16.
HRMS(ESI) M/Z calcd for C14H13O3S. [M + H]+: 261.0580.
Found: 261.0587.
1
1-Phenyl-2-tosylethan-1-one(3b)[8a]: H NMR(400 MHz, CDCl3)
1-Phenyl-2-(thiophen-2-ylsulfonyl)ethan-1-one(3j)[7d]
:
1H
δ 7.94 (d, J = 7.6 Hz, 2H), 7. 76 (d, J = 8.0 Hz, 2H), 7.62 (t, J =
7.6 Hz, 1H), 7.48 (t, J = 7.6 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H),
4.72 (s, 2H), 2.44(s, 3H). 13C NMR(100 MHz, CDCl3) δ 188.39,
145.63, 135.96, 135.93, 134.57, 130.07, 129.57, 129.07, 128.84,
63.79, 21.95. HRMS(ESI) M/Z calcd for C15H15O3S. [M + H]+:
275.0736 . Found: 275.0745.
NMR(400 MHz, CDCl3) δ 7.95 (d, J = 7.6 Hz, 2H), 7.74 (d, J =
4.8 Hz, 1H), 7.70 (d, J = 4.0 Hz, 1H), 7.63 (t, J = 7.2 Hz, 1H),
7.49 (t, J = 7.6 Hz, 2H), 7.14 (t, J = 4.4 Hz, 1H), 4.83 (s, 2H). 13
C
NMR(100 MHz, CDCl3) δ 188.06, 139.60, 135.88, 135.75,
135.24, 134.72, 129.48, 129.16, 128.18, 64.60.HRMS (ESI) M/Z
calcd for C12H11O3S2. [M + H]+: 267.0144. Found: 267.0149.
:
1-Phenyl-2-(propylsulfonyl)ethan-1-one(3k)[8c] 1H NMR(400
MHz, CDCl3) δ 8.01 (d, J = 8.0 Hz, 2H), 7.66 (t, J = 7.2 Hz, 1H),
7.53 (t, J = 8.0 Hz, 2H), 4.56 (s, 2H), 3.26 – 3.22 (m, 2H), 1.99 –
1.86 (m, 2H), 1.11 (t, J = 7.2 Hz, 3H). 13C NMR(100 MHz,
CDCl3) δ 189.58, 136.01, 134.89, 129.57, 129.25, 59.86, 55.60,
16.04, 13.27. HRMS(ESI) M/Z calcd for C11H15O3S. [M + H]+:
227.0736. Found: 227.0740.
[8a]
2-((4-Methoxyphenyl)sulfonyl)-1-phenylethan-1-one (3c)
:
1H NMR(400 MHz, CDCl3) δ 7.95 (d, J = 7.2 Hz, 2H), 7.80 (d, J
= 8.8 Hz, 2H), 7.62 (t, J = 7.6 Hz, 1H), 7.48 (t, J = 7.6 Hz, 2H),
6.98 (d, J = 8.8 Hz, 2H), 4.71 (s, 2H), 3.87 (s, 3H). 13C NMR(100
MHz, CDCl3) δ 188.55, 164.40, 136.04, 134.54, 131.12, 130.43,
129.57, 129.08, 114.61, 64.01, 55.94. HRMS(ESI) M/Z calcd for
C15H15O4S. [M + H]+: 291.0686. Found: 291.0694.

5
2-(Methylsulfonyl)-1-phenylethan-1-one(3l)[7d]
:
1H NMR(400
135.47, 134.73, 129.47, 128.96, 128.82, 64.86. HRMS(ESI)
MHz, CDCl3) δ 8.0 (d, J = 7.6 Hz, 2H), 7.66 (t, J = 7.6 Hz, 1H),
7.53 (t, J = 7.6 Hz, 2H), 4.61 (s, 2H), 3.16 (3, 3H). 13C NMR(100
MHz, CDCl3) δ 189.61, 135.87, 134.96, 129.48, 129.29, 61.53,
42.06. HRMS(ESI) M/Z calcd for C9H11O3S. [M + H]+: 199.0423.
Found: 199.0427.
M/Z calcd for C12H11O3S2. [M + H]+: 267.0144. Found:
267.0149.
1-([1,1'-Biphenyl]-4-yl)-2-tosylethan-1-one
(3u):
m.p.
o
1
107.1~108.5 C, H NMR(400 MHz, CDCl3) δ 7.94 (d, J = 8.4
Hz, 2H), 7.85 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 8.4 Hz, 2H), 7.60
(d, J = 7.2 Hz, 2H), 7.49 (t, J = 7.2 Hz, 2H), 7.43 (t, J = 7.2 Hz,
1H), 7.28 (d, J = 8.0 Hz, 2H), 4.75 (s, 2H), 2.42 (s, 3H). 13C
NMR(100 MHz, CDCl3) δ 187.83, 147.38, 145.90, 139.32,
137.47, 133.59, 129.83, 129.73, 129.39, 129.31, 128.96, 128.02,
127.68, 63.78, 22.03. HRMS(ESI) M/Z calcd for C21H19O3S. [M
+ H]+: 351.1049. Found: 351.1054.
1-(4-Fluorophenyl)-2-(phenylsulfonyl)ethan-1-one(3m) [8a]: H
1
NMR(400 MHz, CDCl3) δ 8.0 (q, J = 5.2 Hz, 2H), 7.88(d, J = 7.6
Hz, 2H), 7.68 (t, J = 7.6 Hz, 1H), 7.56 (t, J = 7.6 Hz, 2H), 7.16 (t,
J = 8.0 Hz, 2H), 4.70 (s, 2H). 13C NMR(100 MHz, CDCl3) δ
186.62, 166.75 (d, J = 257 Hz), 138.80, 134.60, 132.53, 132.43,
129.52, 128.79, 116.39 (d, J = 22 Hz), 63.85. HRMS(ESI) M/Z
calcd for C14H12FO3S. [M + H]+: 279.0486. Found: 279.0480.
1-(4-Chlorophenyl)-2-tosylethan-1-one (3v)[6b]: H NMR (400
1
1-(4-Chlorophenyl)-2-(phenylsulfonyl)ethan-1-one(3n)[8a]
:
1H
MHz, CDCl3) δ 7.89 (d, J = 8.4 Hz, 2H), 7.74 (d, J = 8.4 Hz,
2H), 7.45 (d, J = 8.4 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 4.68 (s,
2H), 2.44 (s, 3H). 13C NMR(100 MHz, CDCl3) δ 187.25, 145.77,
141.29, 135.80, 134.31, 131.00, 130.12, 129.41, 128.76, 63.93,
21.93. HRMS(ESI) M/Z calcd for C21H19ClO3S. [M + H]+:
309.0347. Found: 309.0356.
NMR(400 MHz, CDCl3) δ 7.91 – 7.87 (m, 4H), 7.68 (t, J = 7.6
Hz, 1H), 7.56 (t, J = 7.6 Hz, 2H), 7.50 (d, J = 8.4 Hz, 2H), 4.70
(s, 2H). 13C NMR(100 MHz, CDCl3) δ187.07, 141.42, 138.77,
134.63, 134.28, 130.99, 129.54, 129.49, 128.78, 63.84.
HRMS(ESI) M/Z calcd for C14H12ClO3S. [M + H]+: 295.0190.
Found: 295.0196.
1-(4-Bromophenyl)-2-tosylethan-1-one (3w)[6b] 1H NMR(400
:
1-(4-Bromophenyl)-2-(phenylsulfonyl)ethan-1-one(3o)[8a]
:
1H
MHz, CDCl3) δ 7.81(d, J = 8.0 Hz, 2H), 7.43 (d, J = 8.0 Hz, 2H),
7.63 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 4.67 (s, 2H),
2.45 (s, 3H). 13C NMR(100 MHz, CDCl3) δ 187.50, 145.84,
135.75, 134.71, 132.46, 131.07, 130.22, 130.16, 128.80, 63.96,
21.98. HRMS(ESI) M/Z calcd for C15H14BrO3S. [M + H]+:
352.9842. Found: 352.9836.
NMR(400 MHz, CDCl3) δ 7.87 (d, J = 7.6 Hz, 2H), 7.81 (d, J =
8.4 Hz, 2H), 7.68 (t, J = 7.6 Hz, 1H), 7.62 (d, J = 8.8 Hz, 2H),
7.55 (t, J = 7.6 Hz, 2H), 4.70 (s, 2H). 13C NMR(100 MHz,
CDCl3) δ 187.31, 138.75, 134.65, 134.60, 132.46, 131.00, 130.24,
129.51, 128.75, 63.76. HRMS(ESI) M/Z calcd for C14H12BrO3S.
[M + H]+: 338.9685. Found: 338.9687.
Acknowledgements
[8a]
2-(Phenylsulfonyl)-1-(p-tolyl)ethan-1-one(3p)
:
1H NMR
We gratefully acknowledge the financial support from
Zhejiang Provincial Natural Science foundation of
China (No. LQ16H090004) and the National Natural
Science Foundation of China (No. 31800292). We also
thanks Anna Kerkula for English language editing.
(400 MHz, CDCl3) δ 7.91 (d, J = 7.6 Hz, 2H), 7.85 (d, J = 8.0
Hz, 2H), 7.67 (t, J = 7.6 Hz, 1H), 7.55 (t, J = 7.6 Hz, 2H), 7.28
(d, J = 8.0 Hz, 2H), 4.73 (s, 2H), 2.43 (s, 3H). 13C NMR(100
MHz, CDCl3) δ 187.68, 145.82, 138.98, 134.38, 133.51, 129.77,
129.65, 129.37, 128.77, 63.59, 21.98. HRMS(ESI) M/Z calcd for
C15H15O3S. [M + H]+: 274.0736. Found: 274.0745.
Supplementary data
[8a]
1-(4-Methoxyphenyl)-2-(phenylsulfonyl)ethan-1-one(3q)
:
1H NMR(400 MHz, CDCl3) δ 7.92 (d, J = 9.2 Hz, 2H), 7.88 (d, J
= 7.2 Hz, 2H), 7.66 (t, J = 7.6 Hz, 1H), 7.54 (t, J = 7.6 Hz, 2H),
6.94 (d, J = 8.8 Hz, 2H), 4.68 (s, 2H), 3.88 (s, 3H). 13C NMR(100
MHz, CDCl3) δ 186.38, 164.80, 138.93, 134.40, 132.11, 129.40,
129.04, 128.77, 114.31, 63.62, 55.85. HRMS(ESI) M/Z calcd for
C15H15O4S. [M + H]+: 291.0685. Found: 291.0682.
Experimental procedures, characterization data, and copies of
1H and 13C NMR spectra for all products, Supplementary data
associated with this article can be found in online version at
http://www.sciencedirect.com.
References and notes
1
1-(3-Methoxyphenyl)-2-(phenylsulfonyl)ethanone (3r) [5d]: H
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1-(2-Methoxyphenyl)-2-(phenylsulfonyl)ethanone (3s) [5a]: H
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1H
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Highlights
1. Using water as the solvent, environmental benign and low cost
2. One-pot synthesis, easy and simple operation
3. Wide tolerance of functional groups

Declaration of interests
☒ The authors declare that they have no known competing financial interests or personal relationships
that could have appeared to influence the work reported in this paper.
☐The authors declare the following financial interests/personal relationships which may be considered
as potential competing interests: