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Multicomponent hydrosulfonylation of alkynes for

Cite this: DOI: 10.1039/d3gc02284f
the synthesis of vinyl sulfones†
Lan Mei, Xiao-Rong Shu, Fa-Liang Liu, Jiao-Zhe Li, Jian-Feng Zhang, Keqi Tang *
and Wen-Ting Wei *

Received 26th June 2023,
Accepted 21st September 2023
DOI: 10.1039/d3gc02284f
rsc.li/greenchem
Vinyl sulfones are important structural motifs with a wide range of applications in the biomedical field.
Although the hydrosulfonylations of alkynes have provided straightforward strategies for the synthesis of
vinyl sulfones, these methods still exhibit several drawbacks, such as the use of large amounts of transition
metal catalysts or/and additional additives. Herein, we report an efficient and mild multicomponent reac-
tion (MCR) for the preparation of vinyl sulfones achieved by carrying out hydrosulfonylation of alkynes
with the corresponding aryl diazonium salts, K2S2O5 and thiophenols at room temperature without any
metal catalysts or additives. This transformation was the first example of a thiophenol as a hydrogen
source reacting with vinyl radical with the advantages of high chemoselectivity and step-economy.
Notably, the method was found to also be applicable to aliphatic alkynes, circumventing the limitations of
existing methods, and a gram-scale experiment proceeded smoothly, proving the practicality of the
methodology.

Metal-catalyst-free approaches are promising for the synthesis
of valuable compounds uncontaminated by metal catalysts
with simplified post-treatment processes, and have garnered a
tremendous amount of attention for chemical transform-
ations.1 Moreover, multicomponent reactions (MCRs) have
gradually become a research hotspot in chemistry, due to the
ability to deploy them for constructing multiple chemical
bonds in one pot and rapidly synthesizing complex functional
molecules, thus maximizing the incorporation of starting
materials and avoiding the employment of hazardous and
toxic reagents, as well as minimizing the number of steps and
waste generation.2 Thus, developing metal-catalyst-free MCRs
for the construction of multifunctional molecules has been
highlighted as one of the top challenges in green chemistry.
Vinyl sulfones have attracted considerable interest in
organic chemistry, because they are not only versatile building
blocks in organic synthesis, but also privileged scaffolds that
have been extensively studied in a wide range of biologically
and pharmaceutically active compounds.3 For example, mole-
cules containing vinyl sulfones have been applied as a non-
adenosine triphosphate (ATP) competitive multiple-kinase-tar-
geting anticancer agent (Rigosertib) in phase III clinical trials,
potential drug for the therapy of Parkinson’s disease (Nrf2 acti-
vators), radiation protection agent (Recilisib sodium), cysteine
protease inhibitor (WRR-483), antibacterial agent (BAY 11-
7085) and potent anti-Chagas agent (K11777) (Fig. 1).4 Thus,
the construction of vinyl sulfones remains a long-term goal of
synthetic chemistry due to their unique pharmaceutical
activity and vital synthetic applications.
Over the past few decades, various classic synthetic routes
for the construction of vinyl sulfones have been established,
including the Knoevenagel condensations of sulfonylacetic
acids with aromatic aldehydes,5 Horne–Wadsworth–Emmons
reactions of sulfonyl phosphonates with carbonyl com-
pounds,6 β-elimination of halosulfones or selenosulfones,7
decomposition of tosylhydrazones,8 and oxidation of the
corresponding vinyl sulfides.9 Recently, the cross-coupling/
addition of alkenes/alkynes with sulfonyl derivatives has

School of Materials Science and Chemical Engineering, Institute of Mass

Spectrometry, Ningbo University, Ningbo, Zhejiang, 315211, China.
E-mail: weiwenting@nbu.edu.cn, tangkeqi@nbu.edu.cn
† Electronic supplementary information (ESI) available. CCDC 2267588. For ESI
and crystallographic data in CIF or other electronic format see DOI: https://doi.
org/10.1039/d3gc02284f Fig. 1 Representative vinyl-sulfone-based drug candidates.

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rapidly emerged as an efficient and appealing strategy for the
construction of vinyl sulfones, since alkenes/alkynes are one of
the most abundant and readily available chemical raw
materials and are highly reactive. However, the current conver-
sion methods rely on systems (1) having a transition metal,10
(2) mediated by a strong oxidant,11 (3) using the cooperativity
of a transition metal with oxidant,12 or (4) mediated by base,
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this strategy involving hydrosulfonylation of alkynes
(Scheme 1c), initially forming aryl radicals from aryl diazo-
nium salts, followed by in situ generation of aryl sulfonyl rad-
icals with inexpensive and readily available K2S2O5, and
further synthesis of vinyl sulfones with alkynes via radical
addition and extraction of hydrogen from HAT reagents (RY–H,
Y = S, O, Si). In comparison with existing methods for the syn-

and are limited to activated aryl alkenes13 (Scheme 1a). Yet,
the sulfonylation of alkynes is considered to be one of the
most efficient and straightforward methods for synthesizing
vinyl sulfones (Scheme 1b).10a,e,12b,13c The sustainability and
practicality of these transformations, however, are impacted by
several factors such as their including metal catalysts, stoichio-
metric oxidants, bases and high temperatures. Additionally,
these methods are not applicable to aliphatic alkynes, limiting
the versatility of these preparations of vinyl sulfones. These
reactions have each also been found to severely suffer from
one of the following drawbacks: (1) the need for prefunctiona-
lized coupling partners (such as phenylpropiolic acid),10a,12b
(2) the use of poorly stable and poorly available sulfinic acids
as sulfonyl sources, and (3) the production of harmful
benzene, sulfuric acid, or benzene sulfinates.10e,13c By contrast,
the realization of hydrosulfonylation of alkynes in metal-cata-
lyst-free and additive-free conditions has not yet been reported.
Notably, hydrogen atom transfer (HAT) reagents are widely
used in radical reactions, and especially thiophenols are con-
sidered to be excellent HAT reagents owing to their weak S–H
bond dissociation energy, which can effectively provide hydro-
gen in transformations without the use of metal catalyst.14
Nevertheless, to the best of our knowledge, there are few
reported examples of thiophenols as hydrogen sources used to
directly react with vinyl radicals. Herein, we developed a novel
strategy for the preparation of vinyl sulfone derivatives, with
thesis of vinyl sulfones, the present method has the following
distinctive advantages: (1) metal-catalyst-free and additive-free
reaction at room temperature; (2) highly chemoselective and
step-economical MCR; and (3) the first example of a thiophe-
nol as a hydrogen source reacting with a vinyl radical.
At the outset of our investigation, we used of 4-methyl-
phenylacetylene 1a, 4-methoxybenzenediazonium tetrafluoro-
borate 2a and K2S2O5 3a as the model substrates for evaluating
reaction parameters including solvent, reaction temperature
and substrate dosage (Table 1). We obtained the target hydro-
sulfonylation product 4a in 85% yield by using 4-(trifluoro-
methyl)benzenethiol (1.5 equiv.) as a hydrogen source in 1,2-
dichloroethane (DCE) under N2 at room temperature for 10 h
(entry 1). Notably, the structure of 4a was unambiguously
characterized using X-ray crystallography (CCDC 2267588†). To
further improve the yield of 4a, we screened various solvents
and found that DCE was the best one (entries 2–10). Notably,
we found that this medium-polarity solvent was most favorable
for the reaction and the relatively good solubility of the sub-
strate led to the high yield of the desired product. However,
increasing the reaction temperature from room temperature to
40 °C did not significantly improve the reactivity (entry 11).
Table 1 Screening of optimal reaction conditionsa

Entry Variation from standard reaction conditions Yield of 4ab (%)

1 None 85
2 CHCl3 instead of DCE 84
3 DCM instead of DCE 80
4 MeCN instead of DCE 78
5 THF instead of DCE 57
6 EtOAc instead of DCE 55
7 DMF instead of DCE Trace
8 MeOH instead of DCE 53
9 H2O instead of DCE 8
10 Toluene instead of DCE 45
11 40 °C 87
12 Na2S2O5 instead of 3a 81
13 1.5 equiv. of 3a 71
14 3.0 equiv. of 3a 85
15 1.5 equiv. of 2a 86
16 1.2 equiv. of 4-CF3C6H4SH 72
17 2.0 equiv. of 4-CF3C6H4SH 87
18 O2 instead of N2 11
a
Reaction conditions: 1a (0.2 mmol), 2a (1.2 equiv.), 3a (2.0 equiv.)
Scheme 1 General strategies for the synthesis of vinyl sulfones and and 4-CF3C6H4SH (1.5 equiv.) in DCE (2.0 mL) under N2 at room temp-
hydrosulfonylation of alkynes. erature for 10 h. b Isolated yields.

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Next, 3a was replaced by Na2S2O5 but this replacement did not Table 3 Scope of aryldiazonium tetrafluoroboratesa
exhibit better reactivity (entry 12). In addition, we tested the
amounts of 3a and 2a and found that 2.0 equiv. of K2S2O5 and
1.2 equiv. of 4-methoxybenzenediazonium tetrafluoroborate
were optimal (entries 13–15). Furthermore, we investigated the
amount of 4-(trifluoromethyl)benzenethiol and the results
showed that, from the point of view of atom economy, using
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1.5 equiv. of 4-(trifluoromethyl)benzenethiol was the best

choice (entries 16 and 17). Finally, in the presence of O2 atmo- a
Unless otherwise noted, the reactions were performed with 1
sphere rather than N2, the yield was dramatically reduced (0.2 mmol), 2 (1.2 equiv.), 3a (2.0 equiv.) and 4-CF3C6H4SH (1.5 equiv.)
(entry 18), which may have been due to the oxidation of the in DCE (2.0 mL) under N2 at room temperature for 10 h.
alkyne to ketone by oxygen, thus preventing its further partici-
pation in the reaction.
With the optimal reaction conditions established, we next Table 4 Scope of alkynesa
investigated the scope and limitations of the HAT reagents
(Table 2). A series of substituted aryl and alkyl thiols were
tested. We found that use of the aryl thiols with electron-with-
drawing groups resulted in higher yields than did the use of
that with an electron-donating group. However, when alkyl
thiols were used as HAT reagents under the standard reaction
conditions, only a trace amount of the desired product 4a was
detected, possibly because of the relatively stronger dis-
sociation energy of S–H bonds of alkyl thiols or the effect of
the electron transfer (ET) pathway.14 In addition, when phenol
or triethylsilane was used as the HAT reagent, the yield of the
desired product 4a in each case was extremely low. Eventually,
we discovered that the highest yield of 4a was achieved when
4-(trifluoromethyl)benzenethiol was used as the HAT reagent.
After investigating the scope of HAT reagents, we turned
our attention to assessing the generality of our established
hydrosulfonylation by examining different aryldiazonium tetra-
fluoroborates (Table 3). Various functional groups on the aryl-
diazonium salt were well tolerated and provided the desired
products 4b–4e in good yields. Our experimental results
showed for each of various cases that an aryl diazonium salt
benzene ring bearing an electron-donating group afforded a
a
higher yield of the expected product than did that bearing an Unless otherwise noted, the reactions were performed with 1
electron-withdrawing group. (0.2 mmol), 2a (1.2 equiv.), 3a (2.0 equiv.) and 4-CF3C6H4SH (1.5
equiv.) in DCE (2.0 mL) under N2 at room temperature for 10 h.
Encouraged by the above-described results, we examined
the scope of substituted alkynes under the optimal reaction
conditions (Table 4). As illustrated in Table 4, meta- and ortho-
methyl-substituted aryl alkynes efficiently provided the desired electronic properties of the para-positions of the phenyl substi-
products 4f (84%) and 4g (83%). Then, we tested the various tuents. Regardless of whether the substituents were electron-
donating (–OMe, –nBu, –tBu and –Ph) (4h–4k), electron-neutral
(–H) (4l) or electron-withdrawing groups (–F, –Cl, –Br, –NO2,
Table 2 Scope of HAT reagentsa CF3 and –CHO) (4m–4r), the desired products were observed in
our experiments to be obtained in moderate to good yields
under the standard conditions. In addition to the phenyl
derivatives, the naphthyl and thienyl groups provided the
desired products 4s–4t in 65%–74% yields. Strikingly, the
scope of the reaction could be extended from aryl alkynes to a
variety of aliphatic alkynes. Different straight-chain alkynes
were tested and led to the corresponding hydrosulfonation
a products (4u–4w) in acceptable yields, and we also discovered
Unless otherwise noted, the reactions were performed with 1
(0.2 mmol), 2a (1.2 equiv.), 3a (2.0 equiv.) and HAT reagents (1.5 that 4-phenyl-1-butyne reacted smoothly, affording the desired
equiv.) in DCE (2.0 mL) under N2 at room temperature for 10 h. products 4x in 52% yield. Furthermore, we used internal

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Paper
alkyne diphenylacetylene as the reaction partner, but only a trace
amount of the desired product 4y was detected, possibly due to
the effect of steric hindrance.
To assess the utility and scalability of the developed
approach, we evaluated this hydrosulfonylation of alkynes on a
preparative scale (Table 5). Fortunately, this reaction could be
performed at the 1.0 g scale, affording 4a in 67% yield after
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extending the reaction time to 36 h. Overall, the results illus-
trated the simplicity of the operation and the prospective
utility of this hydrosulfonylation based on the generation of
sulfonyl sources by aryl diazonium salts with K2S2O5 in fine
chemical synthesis.
To gain insight into the possible reaction pathway of the
hydrosulfonylation, mechanistic studies were performed
(Scheme 2). When the radical scavenger 2,2,6,6-tetramethyl-1-
piperidinyloxy (TEMPO) was added to the reaction, the conver-
sion appeared to have been completely inhibited; and TEMPO-
aryl radical adduct 5a was detected using gas chromatography-
mass spectrometry (GC-MS) (Scheme 2a), which confirmed
that the aryl diazonium salts produced aryl radicals during the
reaction. Moreover, a radical clock experiment with (1-cyclo-
propylvinyl)benzene 6a under the standard conditions exclu-
sively furnished the ring-opened product 7a in 79% yield and
Table 5 Gram-scale reactiona
a
Unless otherwise noted, the reactions were performed with 1a
(8.62 mmol), 2a (1.2 equiv.), 3a (2.0 equiv.) and 4-CF3C6H4SH (1.5
equiv.) in DCE (10.0 mL) under N2 at room temperature for 36 h.
Scheme 2 Mechanistic studies.
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Scheme 3 Proposed mechanism.
the coupling product 8a in 82% yield, which demonstrated the
intermediacy of the sulfonyl radical and demonstrated that 4-
(trifluoromethyl)benzenethiol was the source of hydrogen in
this transformation (Scheme 2b).15 Lastly, deuterium labeling
experiments were performed (Scheme 2c): (1) use of D2O
under the standard conditions afforded the mixed H/D
product in 84% yield (27% of D); and (2) including D2O
without 4-(trifluoromethyl)benzenethiol in the reaction did
not work. In addition, when only 4a was reacted in D2O, no
deuterated product was detected. Therefore, from the results
of the isotope labelling experiments, this hydrosulfonylation
was concluded to proceed through an HAT pathway.
On the basis of the above experimental results and the pre-
vious related reports,16–18 a plausible mechanism for this
transformation was derived, and is shown in Scheme 3.
According to this mechanism, initially, the instability of aryl
diazonium salts produces aryl radicals at room temperature,
followed by in situ generation of aryl sulfonyl radicals I with
the release of SO2 from K2S2O5 accompanied by the production
of K2SO3.16 Subsequently, the sulfonyl radical undergoes
radical addition to the alkynes to produce the sulfonylated
vinyl radical intermediate II, which then abstracts the hydro-
gen atom from 4-CF3C6H4SH to afford the final product 4.17
Also, two equivalents of thiyl radicals coupled together from
two consecutive reactions were proposed to produce the di-
sulfide by-product 8a,18 which was isolated and characterized
using nuclear magnetic resonance (NMR) spectroscopy.
Conclusions
In conclusion, we have developed a mild, efficient and practi-
cal hydrosulfonylation of alkynes with aryldiazonium salts,
K2S2O5 and thiophenol, with this reaction proceeding in a
highly chemoselective and step-economical manner at room
temperature under metal-catalyst-free and additive-free con-
ditions, and readily scaled in batch. Mechanistic studies
showed that the thiophenol acts as a HAT reagent in this reac-
tion, and that the hydrogenation of the alkyne proceeds as a
result of a capture of the hydrogen atom from the thiophenol.
Applying this method, both aryl and aliphatic alkynes can
efficiently achieve hydrosulfonylation under mild reaction con-
ditions, delivering a range of high-value vinyl sulfones in mod-
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erate to good yields. Further extensions of this hydrosulfonyla-
tion are still ongoing in our laboratory.
Conflicts of interest
The authors declare no competing financial interest.
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Acknowledgements
We thank the Natural Science Foundation of Zhejiang Province
(No. LY23B020005), the Ningbo Municipal Natural Science
Foundation (No. 2023J070), the Education Foundation of
Zhejiang Province (No. Y202248688), the National Natural
Science Foundation of China (No. U20A20121 and 61971248),
and the Graduate Student Scientific Research and Innovation
Project of Ningbo University (No. IF2022089) for financial
support.
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