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\begin{document}

\title{Electrocatalytic Multicomponent Cascade Cross-Coupling for Synthesis of
Chalcogenosulfonates}



\author[1]{Zhiheng Zhao}%
\author[1]{Hongyan Yan}%
\author[1]{Yaqin Zhou}%
\author[1]{Wei Xue}%
\author[1]{Lijun Gu}%
\author[2]{Shengyong Zhang}%
\affil[1]{Guizhou University}%
\affil[2]{Air Force Medical University}%


\vspace{-1em}



  
  \date{June 14, 2024}


\begingroup
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\selectlanguage{english}
\begin{abstract}
An method for the electrochemical synthesis of chalcogenosulfonates via
a tandem multi-component reaction has been developed. This method is
performed in an undivided cell without the requirement of external
oxidants, acids, and transition metals. A variety of indoles and
sulfinic acid sodium salts can be used in this method, and it is
effective for the late-stage modifications of complex molecules. Not
only thiosulfonates and selenosulfonates but also sulfonotelluroates
could be prepared, making this protocol a useful tool for the
devel-opment of new functional molecules. The afforded products are
promising for pesticide development.%
\end{abstract}%



\sloppy


\textbf{Cite this paper:} \emph{Chin. J. Chem.} \textbf{2023} ,
\emph{41} , XXX---XXX.

\textbf{DOI: 10.1002/cjoc.202300XXX}

Electrocatalytic Multicomponent Cascade Cross-Coupling for Synthesis of
Chalcogenosulfonates

Zhiheng Zhao,\emph{\textsuperscript{a}} Hongyan
Yan,\emph{\textsuperscript{a}} Yaqin Zhou,\emph{\textsuperscript{a}} Wei
Xue,\emph{\textsuperscript{a}} Lijun Gu*\textsuperscript{,\emph{a}} and
Shengyong Zhang\emph{\textsuperscript{b}}

\textsuperscript{a} National Key Laboratory of Green Pesticide, Key
Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry
of Education, Center for R\&D of Fine Chemicals of Guizhou University,
Guizhou, Guiyang, 550025, China.\textsuperscript{b} School of Pharmacy,
Air Force Medical University, Shaanxi, Xi'an, 710032,
China.\textsuperscript{}\selectlanguage{english}
\begin{longtable}[]{@{}l@{}}
\toprule
\textbf{Keywords}\tabularnewline
\midrule
\endhead
Electrophotochemical catalysis \textbar{} multi-component
reaction\textbar{} chalcogenosulfonates\textbar{} antifungal
activity\tabularnewline
\textbf{Comprehensive Summary}\tabularnewline
An method for the electrochemical synthesis of chalcogenosulfonates via
a tandem multi-component reaction has been developed. This method is
performed in an undivided cell without the requirement of external
oxidants, acids, and transition metals. A variety of indoles and
sulfinic acid sodium salts can be used in this method, and it is
effective for the late-stage modifications of complex molecules. Not
only thiosulfonates and selenosulfonates but also sulfonotelluroates
could be prepared, making this protocol a useful tool for the
development of new functional molecules. The afforded products are
promising for pesticide development.\tabularnewline
\bottomrule
\end{longtable}

\section*{}

{\label{section}}

Background and Originality Content

Chalcogenosulfonates-a class of popular chemical reagents-are commonly
used in organic chemistry mainly because they have broad structural
diversity, and unique chemical
reactivity.\textsuperscript{{[}1{]}}Further, they show diverse
biological properties such as antimicrobial and antifungal
activities(Scheme 1a).\textsuperscript{{[}2{]}} In particular,
thiosulfonates and selenosulfonates have attracted considerable research
interest for the construction of novel sulfur- or selenium-containing
compounds(Scheme 1b).\textsuperscript{{[}3{]}} For example, by using
chalcogenosulfonates as bifunctional reagents, various chalcogenative
compounds that contain a two-carbon unit with a heteroatom bonded to
each carbon, have been prepared.\textsuperscript{{[}4{]}} Although
chalcogenosulfonates have played a notable role in the design of
biological active molecules and the development of novel reactions,
their further application is mainly restricted by rare access to
structurally novel chalcogenosulfonates, such as heteroaryl-substituted
or biorelevant chalcogenosulfonates.

\textbf{Scheme 1} (a) Representative bioactive chalcogenosulfonates and
(b) general reaction modes of chalcogenosulfonates

Generally, the strategies for synthesizing thiosulfonates involve two
types of reactions. One method usually relies on the use of substrates
bearing an S--S bond. Examples include the oxidation of disulfides or
thiosulfinates, the nucleophilic substitution of alkali metal
thiosulfonates with alkyl halides, oxiranes or alkenyliodonium
salts.\textsuperscript{{[}5{]}} These methods, however, have many
limitations such as the need for prefunctionalized starting materials,
the use of stoichiometric amounts of oxidants and a narrow substrate
scope. Furthermore, only thiosulfonates could be obtained by this
method. The second approach mainly involves the condensation of sulfonyl
derivatives with other organosulfur/organoselenium
precursors.\textsuperscript{{[}6{]}} However, because of the toxic
reagents, harsh reaction conditions, and the limited availability of
organosulfur/organoselenium precursors, the use of the safe and abundant
sulfur/selenium powder is highly desirable. In addition, the available
techniques are generally limited to synthesizing thiosulfonates or
selenosulfonates, whereas methods to produce sulfonotelluroates remain
rare because the formed C--Te bond can be easily cleaved by metal
catalysts, acids, organolithium reagents,
etc.\textsuperscript{{[}7{]}}Further, the synthesis of
chalcogenosulfonates continues to be very challenging. Thus, because of
these challenges coupled with the increasing importance of
chalcogenosulfonates, synthetic chemists are motivated to develop mild,
general methods that (i) enable efficient incorporation of the simple
chalcogen into the sulfonyl group to form the SO\textsubscript{2}-X (X =
S, Se, Te) bond under transition-metal-, acid-, external-oxidant-free
conditions; and that (ii) are suitable for the facile synthesis of
structurally diverse chalcogenosulfonates and for late-stage
modification of biorelevant compounds.

Organic electrochemistry, in which redox processes are driven with
electric current instead of chemical oxidants or
reductants,\textsuperscript{{[}8{]}} is being increasingly considered in
the past few years for sustainable synthesis owing to its inherent
environmental friendliness, sustainability and
tunability.\textsuperscript{{[}9{]}} Electrochemically catalyzed
multicomponent reactions involving three or more reactants in a one-pot
operation with the incorporate substantial portions of all the
components into the same products,\textsuperscript{{[}10{]}} are green
and efficient and have been used for the construction of chalcogenated
organic compounds.\textsuperscript{{[}11{]}} The synthesis of
chalcogenosulfonates, however, by electrochemically catalyzed
multicomponent reactions has not been realized. Given the importance of
chalcogenosulfonates in the pharmaceutical industry and organic
synthesis, in this study, a simple and efficient method was developed
for the preparation of chalcogenosulfonates from indoles, sulfinic acid
sodium salts and the simple chalcogen, and sulfonotelluroates were
synthesized for the first time via an electrocatalytic three-component
reaction.

\textbf{Scheme 2} Research background and our new observation

Results and Discussion

At the outset of the investigation, Indole \textbf{1a} , sodium\emph{p}
-toluenesulfinate \textbf{2a} and selenium powder were selected as model
substrates (Table 1). After we analyzed a range of reaction parameters,
we discovered that the application of TBAI (n-Bu\textsubscript{4}NI) as
the mediator and supporting electrolyte in a 3:1 mixture of MeCN and
H\textsubscript{2}O with a carbon rod anode and carbon rod cathode under
a constant current (10.0 mA) at room temperature furnished the
selenosulfonate \textbf{3aa} in 89\% yield (entry 1). The screening of
the reaction media revealed that a mixture of MeCN and
H\textsubscript{2}O (2:1) was the most suitable solvent for this
transformation (entries 2---6). Other mediators, such as NaI, KI and
n-Bu\textsubscript{4}NBr, were also well compatible with the present
catalytic reaction delivering the desired product \textbf{3aa} in
moderate yields (entry 7). Different electrode materials and electric
current values did not improve the reaction efficiency (entries 8---11).
A shorter reaction time resulted in 71\% yield of the product
\textbf{3aa} (entry 12). Only a trace amount of product could be
detected when the reaction was performed under an air atmosphere (entry
13). Control experiments revealed that TBAI or electricity was
indispensable, confirming the electrochemical nature of this
three-component reaction (entries 14 and 15). The reaction was scaled up
to a 10-mmol scale, and 72\% yield of the desired product \textbf{3aa}
was obtained by using a single-batch reaction setup (entry 16).

\textbf{Table 1} Optimization of the reaction
conditions\emph{\textsuperscript{a}}\selectlanguage{english}
\begin{longtable}[]{@{}lll@{}}
\toprule
Entry & Variation from the standard conditions & Yield
(\%)\emph{\textsuperscript{b}}\tabularnewline
1 & None & 89\tabularnewline
2 & DMSO/H\textsubscript{2}O (2:1, 6 mL) & 61\tabularnewline
3 & THF/H\textsubscript{2}O (2:1, 6 mL) & 53\tabularnewline
4 & MeCN/H\textsubscript{2}O (3:1, 8 mL) & 80\tabularnewline
5 & MeCN/H\textsubscript{2}O (1:1, 6 mL) & 75\tabularnewline
6 & MeCN (6 mL) & 64\tabularnewline
7 & NaI, NH\textsubscript{4}I, KI, n-Bu\textsubscript{4}NBr instead of
TBAI & 69, 65, 72, 40\tabularnewline
8 & Pt (+) \selectlanguage{romanian}ǀ Pt (-) instead of C (+) ǀ C (-) & 37\tabularnewline
9 & GF (+) \selectlanguage{romanian}ǀ GF (-) instead of C (+) ǀ C (-) & 31\tabularnewline
10 & C (+) \selectlanguage{romanian}ǀ Pt (-) instead of C (+) ǀ C (-) & 50\tabularnewline
11 & 5 mA, 15 mA instead of 10 mA & 42, 80\tabularnewline
12 & 9 h instead of 12 h & 71\tabularnewline
13 & Under air & trace\tabularnewline
14 & Without TBAI & n.d.\tabularnewline
15 & No current & n.d.\tabularnewline
16 & Large-scale reaction & 72\tabularnewline
\bottomrule
\end{longtable}

\textsuperscript{\emph{a}} Reaction conditions: Carbon rod anode (\selectlanguage{ngerman}Ø = 6
mm), carbon rod cathode (Ø = 6 mm), constant current = 10 mA, undivided
cell, \textbf{1a} (0.5 mmol), \textbf{2a} (0.8 mmol), Se (0.6 mmol),
TBAI (0.5 mmol), MeCN (4 mL), H\textsubscript{2}O (2 mL), room
temperature, N\textsubscript{2}, 12 h, n.d. = not
detected.\textsuperscript{\emph{b}} Isolated yield.

After the optimal reaction conditions were identified, the scope of
indoles was investigated. An array of structurally diverse indoles
participated in this transformation. Indoles with electron-donating
groups at the phenyl ring, including 5-methoxy (\textbf{3ab} ), 3-, 6-,
and 7-methyl-substituted indoles, proceeded smoothly to give
selenosulfonates (\textbf{3ac} ---\textbf{3ae} ) with good to high
yields (62\%---86\%). Notably, 6-benzyloxy substituted indole was
successfully applied in the reaction (\textbf{3af} ). Moreover, indoles
bearing electron-withdrawing groups on the phenyl ring gave good product
yields (\textbf{3ag} ---\textbf{3ai} ). Further, the
3-methyl-substituted indole reacted to give product (\textbf{3aj} ) in
60\% yield. Interestingly, N-methyl-indole (\textbf{3ak} ),
dihydroquinoline (\textbf{3al} ), and N-phenyl-indole (\textbf{3am} )
were viable substrates. Moreover, benzothiophene was well-tolerated in
this transformation (\textbf{3an} ), indicating the wide range of
applicability of the method. In addition, the electrochemical protocols
accommodated indole precursors with motifs, such as gemfibrozil,
ibuprofen, and dicamba, giving the corresponding selenosulfonates
(\textbf{3ao} ---\textbf{3aq} ) in good yields. These results highlight
the potential practical applications of this method for the late-stage
modification of pharmaceutical-related molecules.

\textbf{Scheme 3} Scope of indoles\emph{\textsuperscript{a,b}}

\emph{\textsuperscript{a}} Reaction conditions: Carbon rod anode (Ø = 6
mm), carbon rod cathode (Ø = 6 mm), constant current = 10 mA, undivided
cell, \textbf{1} (0.5 mmol), \textbf{2a} (0.8 mmol), Se (0.6 mmol), TBAI
(0.5 mmol), MeCN (4 mL), H\textsubscript{2}O (2 mL), room temperature,
N\textsubscript{2}, 12 h. \emph{\textsuperscript{b}} Isolated yield.

Next, we examined the generality of this electrocatalytic
three-component reaction with respect to a range of sulfinic acid sodium
salts \textbf{2} (Scheme 4). Halogen functionalities, F and Cl, remain
intact after reaction (\textbf{3ba} and \textbf{3bc} ), thereby offering
easy handles for controlled installation of other peripheral functional
groups at the halogenated positions. The application of benzenesulfinic
acid sodium salt gave the desired products in 87\% yield (\textbf{3bd}
). Notably, sulfinic acid sodium salts bearing fused rings and
heteroaryl moieties were also employed in this reaction and gave
products (\textbf{3be} and \textbf{3bf} ) with satisfactory yields.
Notably, the alkyl-substituted sulfinic acid sodium salt was well
incorporated and the corresponding product (\textbf{3bg} ) was obtained
in 63\% yield.

\textbf{Scheme 4} Scope of sulfinic acid sodium salts

\emph{\textsuperscript{a,b}}

\emph{\textsuperscript{a}} Reaction conditions: Carbon rod anode (Ø = 6
mm), carbon rod cathode (Ø = 6 mm), constant current = 10 mA, undivided
cell, \textbf{1a} (0.5 mmol), \textbf{2} (0.8 mmol), Se (0.6 mmol), TBAI
(0.5 mmol), MeCN (4 mL), H\textsubscript{2}O (2 mL), room temperature,
N\textsubscript{2}, 12 h. \emph{\textsuperscript{b}} Isolated yield.

To showcase the application of this methodology, the electrocatalytic
three-component reaction was examined by using indoles \textbf{1} ,
sulfinic acid sodium salts \textbf{2} and sulfur powder as substrates
under the standard conditions to prepare thiosulfonates (Scheme 5).
Notably, indoles \textbf{1} bearing functional groups at the aryl ring
(\textbf{4aa} ), such as OMe (\textbf{4ab} and \textbf{4ac} ), Me
(\textbf{4ad} ), or F (\textbf{4ae} ), efficiently participated in the
reaction. In addition, benzothiophen was also well compatible with this
methodology (\textbf{4af} ). Notably, cyclohexyl-substituted sodium
sulfinate was well-suited for this transformation (\textbf{4ag} ).

\textbf{Scheme 5} Synthesis of thiosulfonates

\emph{\textsuperscript{a,b}}

\emph{\textsuperscript{a}} Reaction conditions: Carbon rod anode (Ø = 6
mm), carbon rod cathode (Ø = 6 mm), constant current = 10 mA, undivided
cell, \textbf{1} (0.5 mmol), \textbf{2} (0.8 mmol), S (0.6 mmol), TBAI
(0.5 mmol), MeCN (4 mL), H\textsubscript{2}O (2 mL), room temperature,
N\textsubscript{2}, 12 h. \emph{\textsuperscript{b}} Isolated yield.

As mentioned above, many examples of the synthesis of thiosulfonates and
selenosulfonates are presented in the literature, but the methods to
synthesize sulfonotelluroates remains a challenge. Our proposed
electrocatalytic three-component reaction could be extended to the
synthesis of sulfonotelluroates using elemental tellurium as the
tellurium source (Scheme 6). Under the modified
conditions,\textsuperscript{{[}12{]}} sulfonotelluroate \textbf{5aa} was
obtained in 76\% yield by the reaction of indole \textbf{1a} ,
sodium\emph{p} -toluenesulfinate \textbf{2a} , and elemental tellurium.
Moreover, the electronic characteristics and positional variations of
substituents on the phenyl ring of indoles have no effect on the product
yield. Further, an array of structurally diverse indoles can
successfully participate in this cascade cross-coupling. Further,
various functional groups such as Me, OMe, and NO\textsubscript{2} can
be well-suited for this transformation (\textbf{5ab} ---\textbf{5af} ).
Interestingly, benzothiophen also gave the corresponding product
(\textbf{5ag} ) in 47\% yield, and N-ethyl-indole gave the desired
product (\textbf{5ah} ) in 62\% yield. Further, in this method,
cyclopropyl or 4-chlorophenyl-substituted sodium sulfinates could be
used as coupling partners, resulting in the efficient for-mation of
corresponding sulfonotelluroates (\textbf{5ai} and \textbf{5aj} ).

\textbf{Scheme 6} Synthesis of sulfonotelluroates

\emph{\textsuperscript{a,b}}

\emph{\textsuperscript{a}} Reaction conditions: Carbon rod anode (Ø = 6
mm), Carbon rod cathode (Ø = 6 mm), constant current = 12 mA, undivided
cell, \textbf{1} (0.5 mmol), \textbf{2} (0.8 mmol), Te (0.6 mmol),
Cs\textsubscript{2}CO\textsubscript{3} (0.8 mmol), TBAI (0.5 mmol), MeCN
(4 mL), H\textsubscript{2}O (2 mL), Room temperature,
N\textsubscript{2}, 12 h. \emph{\textsuperscript{b}} Isolated yield.

To gain some insight into the mechanism of the electrocatalytic
multicomponent reaction, some controlled experiments were conducted with
elemental selenium as an example, as depicted in Scheme 7. First,
without indole \textbf{1a} , the reaction of Na-salt \textbf{2a} with
elemental selenium under the standard conditions did not produce
Na-salt\textbf{2a-I} , suggesting that \textbf{2a-I} might not be
involved in the process (Scheme 7A). Next, to validate the Ts\selectlanguage{english}*and I\selectlanguage{english}*
radical intermediates, a reaction was carried out with standard
conditions using ethene-1,1-diyldibenzene as the trapping reagent. The
compounds\textbf{1aa-I} and \textbf{1aa-II} were detected by
high-resolution mass spectrometry (Scheme 7B). Furthermore, when
sodium\emph{p} -toluenesulfinate \textbf{2a} and elemental selenium
reacted with styrene under the standard conditions (Scheme 7C),
(\emph{E} )-Se-styryl 4-methylbenzenesulfonoselenoate (\textbf{3ar} )
was obtained in 67\% yield; further, a diselenide could be detected by
gas chromatography (GC), indicating that radical TsSe\selectlanguage{english}* may be the
intermediate in this transformation (Scheme 7D).

\textbf{Scheme 7} Investigation of the mechanism

In addition, we also conducted a series of cyclic voltammetry (CV)
experiments (Figure 1). In the case of TBAI, an oxidation peak occurred
at 0.46 V vs. Ag/AgCl (SCE), corresponding to the electro-oxidation of
I\selectlanguage{english}\textsuperscript{-} ions. Sodium \emph{p} -tolylsulfinate
\textbf{2a}easily lost a single electron and the oxidation potential was
observed at 0.74 V \emph{vs.} Ag/AgCl (SCE). No apparent oxidation peak
corresponding to Se was visible in the region of 0.0--2.0 V, so Se
oxidization on the anode can be ruled out (Figure 1, curve c). Curve d
shows an oxidation peak for indole \textbf{1a} at 1.32 V. However, in
the absence of TBAI, no desired product \textbf{3aa} could be detected
(Table 1, entry 14), which might exclude \textbf{1a'} as the
intermediate of this electrocatalytic transformation (Scheme 7E).\selectlanguage{english}
\begin{figure}[H]
\begin{center}
\includegraphics[width=0.70\columnwidth]{figures/image14/image14}

\end{center}
\end{figure}

\textbf{Figure 1} CV of 0.1mol/L of LiClO\textsubscript{4} in 4 mL of
MeCN and 2 mL of H\textsubscript{2}O solution containing different
compounds: (a) blank experiment; (b) Sodium \emph{p}
-tolylsulfinate\textbf{2a} (0.8 mmol); (c) Se (0.6 mmol); (d) Indole
\textbf{1a} (0.5 mmol); (e) TBAI (0.5 mmol); (f) Sodium \emph{p}
-tolylsulfinate\textbf{2a} (0.8 mmol), Se (0.6 mmol), Indole \textbf{1a}
(0.5 mmol), TBAI (0.5 mmol); with a GC disk working electrode, Pt
counter electrode, and Ag/AgCl reference electrode at 0.01 V/s scan
rate.

Based on these findings and those of previous
studies,\textsuperscript{{[}13{]}} we propose the reaction mechanism
depicted in Scheme 8. Initially, single-electron-transfer (SET)
oxidation of \textbf{2a} at the anode generates a sulfonyl
radical\textbf{A} that reacts with elemental selenium to generate the
free radical intermediate TsSe* (\textbf{B} ). Subsequently, the radical
addition of \textbf{1a} with intermediate \textbf{B} gives the radical
species \textbf{C} . Then 3-iodoindoline \textbf{E} is obtained through
radical cross-coupling of \textbf{C} and the iodine radical from the
anodic oxidation of iodine ions. Alternatively, SET oxidation
of\textbf{C} at the anode produces the cation intermediate \textbf{D}
that is quickly attacked by I\textsuperscript{--} to give
intermediate\textbf{E} . Subsequent elimination of HI could afford the
desired product \textbf{3aa} .

\textbf{Scheme 8} Plausible reaction mechanism

Owing to the unique scaffolding of chalcogenosulfonates, we envision
that the obtained compounds will serve as a promising platform for the
design and discovery of fungicides. A total of 28 chalcogenosulfonates
were tested for \emph{in vitro} antifungal activity against two
phytopathogenic fungi at 100 \selectlanguage{greek}\emph{μ} \selectlanguage{english}g/L, using commercialized
fungicide azoxystrobin as positive control agent. As shown in the
Supplementary Information (Table S5), compounds \textbf{3ag} (79.5\%
inhibition),\textbf{3ai} (81.2\% inhibition), \textbf{3al} (82.2\%
inhibition),\textbf{3bf} (83.4\% inhibition), \textbf{4ae} (79.1\%
inhibition), and\textbf{5ag} (79.7\% inhibition) showed better
antifungal activities than azoxystrobin (78.5\% inhibition) against
\emph{Botrytis. cinerea} . Notably, compounds \textbf{3ag} (86.4\%
inhibition), \textbf{3ai}(89.4\% inhibition), \textbf{3al} (92.6\%
inhibition), \textbf{3bf}(90.2\% inhibition), \textbf{4ae} (87.9\%
inhibition), and \textbf{5ag}(85.5\% inhibition) showed potent
antifungal activities that were higher than the activities of
azoxystrobin (85.3\% inhibition) against\emph{Rhizoctonia. solani} .

To better understand the antifungal activities of these compounds, the
half maximal effective concentration (EC\textsubscript{50}) values of
compounds with more than 75\% inhibition rate at 100 \selectlanguage{greek}μ\selectlanguage{english}g/L were
considered (Figure 2). Compounds \textbf{3ai} and \textbf{4ae} showed
the best antifungal activities among 28 chalcogenosulfonates, and their
EC\textsubscript{50} values were much lower than those of commercial
azoxystrobin pesticides. These findings enable the adoption of a new
course in studying the biological activity of chalcogen-containing
organic compounds.\selectlanguage{english}
\begin{figure}[H]
\begin{center}
\includegraphics[width=0.70\columnwidth]{figures/image16/image16}

\end{center}
\end{figure}

\textbf{Figure 2} EC\textsubscript{50} values of compounds with good
antifunal activities against \emph{B. cinerea} and \emph{R.
solani\textsuperscript{a}}

Conclusions

In summary, we have developed a transition-metal-, acid- and
external-oxidant-free method for the synthesis of chalcogenosulfonates
from readily available starting materials. Indoles and sulfinic acid
sodium salts bearing different substitution patterns are involved in
this transformation. The mild conditions and the tolerance to a wide
variety of functional groups permit the derivatization of complex
indoles. To our knowledge, this is the first example of the construction
of sulfonotelluroates. The afforded chalcogenosulfonates showed
promising practical applications in pesticide development.

Experimental

\textbf{General procedure for synthesis of (3)}

A 10-mL undivided three-necked bottle was equipped with a carbon rod
anode (\selectlanguage{ngerman}Ø = 6 mm) and carbon rod cathode (Ø = 6 mm) which was connected
to a direct current (DC) regulated power supply. \textbf{1} (0.5 mmol),
selenium powder (0.6 mmol), \textbf{2} (0.8 mmol), and TBAI (0.5 mmol)
were dissolved in 4 mL MeCN and 2 mL H\textsubscript{2}O, the cell was
electrolyzed at a constant current of 10 mA (\textasciitilde{}9.2
mA/cm\textsuperscript{2}). The mixture was stirred for 10 h at
environment temperature. The electrolysis was terminated when the
starting materials were consumed as determined by TLC. Then the reaction
mixture was diluted with 50 mL ethyl acetate, washed with a saturated
solution of brine (2 × 15 mL), dried
(Na\textsubscript{2}SO\textsubscript{4}), and concentrated in vacuum,
and the resulting residue was purified by silica gel column
chromatography (eluent: petroleum ether/ethyl acetate) to afford the
desired products \textbf{3} .

Supporting Information

The supporting information for this article is available on the WWW
under https://doi.org/10.1002/cjoc.2023xxxxx.

Acknowledgement

We acknowledge funding supports from the starting grant of Guizhou
University {[}(2023)5){]}. We also thank International Science Editing
for editing this manuscript.

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\end{enumerate}\selectlanguage{english}
\begin{longtable}[]{@{}lll@{}}
\toprule
Manuscript received: XXXX, 2023 Manuscript revised: XXXX, 2023
Manuscript accepted: XXXX, 2023 Accepted manuscript online: XXXX, 2023
Version of record online: XXXX, 2023 & &\tabularnewline
\bottomrule
\end{longtable}

The Authors\selectlanguage{english}
\begin{longtable}[]{@{}lll@{}}
\toprule
& After acceptance, please insert a group photo of the authors taken
recently. &\tabularnewline
& \textbf{Left to Right:} Authors Names &\tabularnewline
\bottomrule
\end{longtable}

\textbf{Entry for the Table of Contents}\selectlanguage{english}
\begin{longtable}[]{@{}l@{}}
\toprule
\textbf{An Electrocatalytic Multicomponent Cascade
Cross-Coupling:Facile Access to Chalcogenosulfonates} Zhiheng Zhao,
Hongyan Yan, Yaqin Zhou, Wei Xue, Lijun Gu,* and Shengyong Zhang
\emph{Chin. J. Chem.} \textbf{2023}, \emph{41}, XXX---XXX. \textbf{DOI:
10.1002/cjoc.202300XXX}\tabularnewline
An electrocatalytic multicomponent cascade cross-coupling for the
synthesis of chalcogenosulfonates under transition-metal-, acid- and
external-oxidant-free conditions in an undivided cell has been
developed. The afforded chalcogenosulfonates showed promising practical
applications in pesticide development.\tabularnewline
\bottomrule
\end{longtable}

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