A Concise Route to 2-Sulfonylacetonitriles from Sodium Metabisulfite

Article abstract of DOI:10.1002/adsc.202001243

A three-component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and 3-azido-2-methylbut-3-en-2-ol under mild conditions is described. By using abundant and cheap sodium metabisulfite as the sulfur dioxide surrogate, this protocol features good functional group compatibility, affording 2-arylsulfonylacetonitriles in moderate to good yields. The reaction proceeds smoothly at room temperature without the need of any catalysts or additives. Moreover, the synthetic utility of this method is demonstrated by the transformation of 2-arylsulfonylacetonitrile into 2-arylsulfonyl acetamide and 2-arylsulfonylethylamine. (Figure presented.).

Full text of DOI:10.1002/adsc.202001243

Title: A Concise Route to 2-Sulfonylacetonitriles from Sodium
Metabisulfite
Authors: Yanfang Yao, Ziqing Yin, Weiyun Chen, Wenlin Xie, Fu-
Sheng He, and Jie Wu
This manuscript has been accepted after peer review and appears as an
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.202001243
Link to VoR: https://doi.org/10.1002/adsc.202001243

10.1002/adsc.202001243
Advanced Synthesis & Catalysis
UPDATE
DOI: 10.1002/adsc.202((will be filled in by the editorial staff))
A Concise Route to 2-Sulfonylacetonitriles from Sodium
Metabisulfite
Yanfang Yao,a Ziqing Yin,b Weiyun Chen,b Wenlin Xie,*a Fu-Sheng He,*b and Jie
Wu*b,c
a
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201,
China.
E-mail: xwl2000zsu@163.com
School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu
b
Avenue, Taizhou 318000, China.
E-mail: 0618006@zju.edu.cn; jie_wu@fudan.edu.cn
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of
c
Sciences, 345 Lingling Road, Shanghai 200032, China.
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
In the past decade, synthesis of sulfonyl compounds
with the insertion of sulfur dioxide has received
considerable attention due to its low toxicity and easy
operation.[6] Sulfur dioxide surrogates including
DABCO·(SO2)2 (1,4-diazabicyclo[2.2.2]octane-sulfur
dioxide) and inorganic sulfites have been widely
employed as alternatives to gaseous sulfur dioxide.[7,8]
Specifically, it was found that unstable carbon-
centred radical could be trapped by sulfur dioxide to
produce sulfonyl radical for the construction of
sulfonyl compounds. So far, significant achievements
have been witnessed in this field.[9] For example, by
using sodium metabisulfite as the source of sulfur
dioxide, photoinduced sulfonylation of 2,2-difluoro
enol silyl ethers to access α, α-difluoro-β-ketosulfones
was developed recently.[10]
Abstract. A three-component reaction of aryldiazonium
tetrafluoroborates, sodium metabisulfite, and 3-azido-2-
methylbut-3-en-2-ol under mild conditions is described. By
using abundant and cheap sodium metabisulfite as the sulfur
dioxide surrogate, this protocol features good functional
group compatibility, affording 2-arylsulfonylacetonitriles in
moderate to good yields. The reaction proceeds smoothly at
room temperature without the need of any catalysts or
additives. Moreover, the synthetic utility of this method is
demonstrated
by
the
transformation
of
2-
arylsulfonylacetonitrile into 2-arylsulfonyl acetamide and 2-
arylsulfonylethylamine.
Keywords: 2-sulfonylacetonitrile; sulfur dioxide insertion;
radical; sulfonylation
On the other hand, we noticed that Donald and co-
workers developed a photoredox methodology for the
sulfonyl radical-mediated cyanomethylation of 3-
azido-2-methylbut-3-en-2-ol via vinyl azide cascade-
fragmentation, leading to 2-arylsulfonylacetonitriles
in good yields.[11] In this transformation, toxic sulfonyl
chlorides were employed for the generation of sulfonyl
radicals. Recently, an alternative route for the
It is well known that sulfones are key structural
motifs in numerous biologically active compounds and
pharmaceutical intermediates.[1] In particular, 2-
arylsulfonylacetonitriles are important building blocks
not only in organic chemistry but also in medicinal
chemistry.[2] For instance, β-aminonitriles and β-keto
sulfones synthesized from 2-arylsulfonylacetonitriles
can be converted to pesticides, medicine and feed
additives.[3] Additionally, 2-(arylsulfonyl)acetonitriles
photoinduced
synthesis
of
2-
(arylsulfonyl)acetonitriles from aryl iodides under
ultraviolet irradiation was described.[12] However, the
requirement of special set-up for ultraviolet light
limited its further application. Additionally, the
substrate scope was narrow due to ultraviolet light
irradiation. To address the above issues, herein, we
report a mild sulfonylation reaction of 3-azido-2-
methylbut-3-en-2-ol at room temperature without the
need of ultraviolet irradiation or any catalysts. By
using the abundant and cheap sodium metabisulfite as
the sulfur dioxide surrogate, this protocol features
have
been
used
in
the
synthesis
of
triazolothienopyrimidine UT-B inhibitors, which can
selectively and reversibly inhibit urea transport and
reduce urinary concentration in mic.[4] However,
traditional methods for the preparation of 2-
(arylsulfonyl)acetonitriles often suffer from using
sulfonic acids or salts, thiophenols, haloacetonitriles,
or harsh conditions that require oxidants and additional
steps (Scheme 1a).[5] Therefore, development of mild
and green sulfonylation reactions to 2-
arylsulfonylacetonitriles is highly desirable.
1
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10.1002/adsc.202001243
Advanced Synthesis & Catalysis
e)
good functional group compatibility, affording 2-
arylsulfonylacetonitriles in moderate to good yields.
Initially, we began our investigations by exploring
the model reaction of 4-methylphenyldiazonium
tetrafluoroborate 1a, DABCO·(SO2)2, and 3-azido-2-
methylbut-3-en-2-ol 2a. To our delight, the reaction
proceeded smoothly in 1,2-dichloroethane (DCE)
without the need of any catalysts or additives,
affording the desired product 3a in 46% yield (Table
1, entry 1). Encouraged by this result, the source of
sulfur dioxide was then evaluated (Table 1, entries 2-
3). Interestingly, the yield of compound 3a was
increased to 64% by using sodium metabisulfite as the
sulfur dioxide surrogate (Table 1, entry 3). After a
survey of various solvents including CH3CN, CH2Cl2,
DMF and a mixture of DCE/CH3CN, we found that no
better results was obtained (Table 1, entries 4-7).
Subsequently, we shifted our attention to investigate
the effect of reaction temperature. It was found that
changing the reaction temperature led to unsatisfactory
yields of product 3a (Table 1, entries 8-9).
Gratifyingly, the yield of compound 3a was increased
to 72% when the amount of 4-methylphenyldiazonium
tetrafluoroborate 1a and 3-azido-2-methylbut-3-en-2-
ol 2 was exchanged (Table 1, entry 10). Moreover,
variation of the alcohol derived vinyl azides with other
substituents 2b-2e showed that dimethyl alcohol
derived vinyl azide 2a was still the best choice (Table
1, entries 11-14).
mmol), 3-azido-2-methylbut-3-en-2-ol 2a (0.3 mmol).
Compound 2b instead of 2a. f) Compound 2c instead of 2a.
Compound 2d instead of 2a. Compound 2e instead of
2a.
g)
h)
With the above optimized conditions in hand, we
further evaluated the scope generality of this three-
component reaction of aryldiazonium
tetrafluoroborates 1, sodium metabisulfite and 3-
azido-2-methylbut-3-en-2-ol 2. The result is shown in
Table 2. Various aryldiazonium tetrafluoroborates 1
were employed under the conditions, and a variety of
electron-donating or electron-withdrawing groups
attached on the aromatic ring of aryldiazonium
tetrafluoroborates were found to be compatible in this
transformation. All reactions proceeded well, leading
to the corresponding products 3 in moderate to good
yields. For instance, substrates bearing methyl,
methoxyl and methylthio groups at the para position
of aryldiazonium tetrafluoroborates gave rise to the
desired products 3a-3d in 66-78% yields. Moreover,
the para-cyano substituted substrate was also tolerated
in this transformation, affording product 3n with
dinitrile groups, albeit with moderate yield. The
naphthyl substituted 2-sulfonylacetonitriles 3q-3r
were obtained in 46-48% yields. Notably, this
procedure could be extended to heterocyclic-
substituted diazonium tetrafluoroborates, giving rise to
thiophene substituted 2-sulfonylacetonitrile 3s in 23%
yield. The formation of thiophene-substituted
acetonitrile as the major byproduct caused low
reaction efficiency, which could be detected by LC-
MS from the reaction mixture. The corresponding
Table 1. Initial studies for the synthesis of 2-
sulfonylacetonitriles with the insertion of sulfur dioxide [a]
pyrazole
and
quinoline
substituted
2-
sulfonylacetonitriles 3t and 3u were obtained in 54%
and 40% yields, respectively. Additionally, this
protocol could be extended to disubstituted diazonium
tetrafluoroborates, providing the desired products 3v-
3z in 40-75% yields.
Yield[b]
(%)
Entry
“SO2”
Solvent
Temp. (°C)
Table 2. Scope exploration for the synthesis of 2-
sulfonylacetonitriles with the insertion of sulfur dioxide [a]
1
2
3
4
5
DABSO
K2S2O5
Na2S2O5
Na2S2O5
Na2S2O5
Na2S2O5
Na2S2O5 DCE/CH3CN
Na2S2O5
Na2S2O5
DCE
DCE
DCE
CH3CN
CH2Cl2
DMF
25
25
25
25
25
25
25
0
50
25
25
25
25
25
46
62
64
56
63
38
63
trace
36
72
37
65
70
6
7[c]
8
DCE
DCE
DCE
DCE
DCE
DCE
DCE
9
10[d] Na2S2O5
11[e] Na2S2O5
12[f] Na2S2O5
13[g] Na2S2O5
14[h] Na2S2O5
Reaction
71
a)
conditions:
4-methylphenyldiazonium
tetrafluoroborate 1a (0.3 mmol), “SO2” (0.4 mmol), 3-
azido-2-methylbut-3-en-2-ol 2a (0.2 mmol), solvent (2.0
mL), N2, room temperature. b) Isolated yield. c) Solvent ratio
(1:1). d) 4-Methylphenyldiazonium tetrafluoroborate 1a (0.2
2
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10.1002/adsc.202001243
Advanced Synthesis & Catalysis
Subsequently, several control experiments were
performed to gain more insight into the mechanism of
this reaction (Scheme 2). The sulfonylation process
was hampered completely when radical inhibitor
TEMPO was introduced into the model reaction of 4-
methylphenyldiazonium
tetrafluoroborate
1a,
DABCO·(SO2)2, and 3-azido-2-methylbut-3-en-2-ol 2
(Scheme 2, eqn a). Furthermore, 1,1-diphenylethylene
was employed in the model reaction under the optimal
conditions, giving rise to product 3a in 33% yield, and
(2-(p-tolyl)ethene-1,1-diyl)dibenzene 5 was detected
by GC-MS (Scheme 2, eqn b). These resluts suggested
that sulfonyl radical was involved in this
transformation. The desired product 3a and
benzophenone 8 were isolated in 50% and 99% yields
respectively,
when
the
reaction
of
4-
methylphenyldiazonium tetrafluoroborate 1a, sodium
metabisulfite and 2-azido-1,1-diphenylprop-2-en-1-ol
7 was performed under the standard conditions
(Scheme 2, eqn c). This outcome showed that the
reaction would undergo C-C bond cleavage to afford
the desired product.
a Isolated yield based on aryldiazonium tetrafluoroborate 1.
To demonstrate the synthetic utility of this protocol,
further transformations of 2-arylsulfonylacetonitriles
were carried out. For instance, treatment of product 3a
in the presence of concentrated H2SO4 afforded 2-
arylsulfonyl acetamide 4 in 89% yield (Scheme 1, eqn
1). Additionally, reduction of compound 3a by NaBH4
and NiCl2 produced N-Boc 2-arylsulfonylethylamine 5
in 71% yield (Scheme 1, eqn 2).
Scheme 2. Control experiments.
Therefore,
a
plausible mechanism for this
sulfonylation process was proposed on the basis of
previous reports5-10 and the above mechanistic studies
(Scheme 3). We reasoned that initially, arylsulfonyl
radical A would be generated in situ from the reaction
of aryldiazonium tetrafluoroborate 1 and sodium
metabisulfite. Subsequently, addition of arylsulfonyl
radical A to 3-azido-2-methylbut-3-en-2-ol would
give rise to radical intermediate B. Followed by release
of nitrogen, radical intermediate C would be produced.
This radical intermediate C would further undergo C-
C bond cleavage to provide arylsulfonylacetonitrile 3
and ketyl radical D. Consequently, acetone was
formed as the byproduct through the deprotonation of
ketyl radical D.
Scheme 1. Transformations of 2-sulfonylacetonitrile 3a.
3
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10.1002/adsc.202001243
Advanced Synthesis & Catalysis
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In summary, we have presented a facile route to 2-
arylsulfonylacetonitriles by using abundant, cheap and
readily available sodium metabisulfite as the sulfur
dioxide surrogate in the reaction of aryldiazonium
tetrafluoroborates and 3-azido-2-methylbut-3-en-2-ol.
This transformation proceeds efficiently at room
temperature without the need of ultraviolet irradiation
irradiation, additives or any catalysts, providing 2-
arylsulfonylacetonitriles in moderate to good yields
under mild conditions. Moreover, the resulting 2-
arylsulfonylacetonitriles can be readily converted into
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2-arylsulfonylacetamide
and
2-
arylsulfonylethylamine. Preliminary mechanistic
studies reveal that arylsulfonyl radical generated in
situ from aryldiazonium tetrafluoroborate and sodium
metabisulfite would react with 3-azido-2-methylbut-3-
en-2-ol to give the corresponding product.
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Experimental Section
General experimental procedure for the synthesis of 2-
sulfonylacetonitriles
3-Azido-2-methylbut-3-en-2-ol 1 (0.3 mmol) was added to
a mixture of aryldiazonium tetrafluoroborate 2 (0.2 mmol),
Na2S2O5 (0.4 mmol) in DCE (2.0 mL) under N2 atmosphere.
The mixture was stirred at room temperature for 8 h. After
completion of reaction as indicated by TLC, the solvent was
evaporated and the residue was purified directly by flash
column chromatography (n-hexane/ethyl acetate = 4:1) to
give the corresponding product 3.
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Acknowledgements
Financial support from the National Natural Science Foundation
of China (Nos. 21871053 and 21532001) and the Leading
Innovative and Entrepreneur Team Introduction Program of
Zhejiang (No. 2019R01005) is gratefully acknowledged. We thank
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5
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10.1002/adsc.202001243
Advanced Synthesis & Catalysis
UPDATE
A Concise Route to 2-Sulfonylacetonitriles from
Sodium Metabisulfite
Adv. Synth. Catal. Year, Volume, Page – Page
Yanfang Yao,a Ziqing Yin,b Weiyun Chen,b Wenlin
Xie,*a Fu-Sheng He,*b and Jie Wu*b,c
6
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