Electrochemical Three-Component Synthesis of β,β-Dialkoxy Sulfides from Terminal Alkynes, Thiophenols, and Alcohols

doi:10.6023/cjoc202602004

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (6): 2399-2408.DOI: 10.6023/cjoc202602004 Previous Articles Next Articles

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电化学促进芳香炔、芳基硫酚和醇三组分合成β,β-二烷氧基硫醚

张文升^a^,^b, 张建航^b, 刘建明^b^,^*(), 汤清虎^b^,^*()

^a 洛阳文化旅游职业学院教育学院河南洛阳 471000
^b 河南师范大学化学化工学院绿色化学介质与反应省部共建教育部重点实验室河南新乡 453007

收稿日期:2026-02-03 修回日期:2026-03-22 发布日期:2026-04-13
基金资助:
河南省自然科学基金(262300421690); 河南省高等学校重点科研项目计划基础研究专项(26ZX009)

Electrochemical Three-Component Synthesis of β,β-Dialkoxy Sulfides from Terminal Alkynes, Thiophenols, and Alcohols

Wensheng Zhang^a^,^b, Jianhang Zhang^b, Jianming Liu^b^,^*(), Qinghu Tang^b^,^*()

^a Education College, Luoyang Vocational College of Culture and Tourism, Luoyang, Henan 471000
^b Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, College of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2026-02-03 Revised:2026-03-22 Published:2026-04-13
Contact: * E-mail: jmliu@htu.cn;tangqinghu@htu.edu.cn
Supported by:
Natural Science Foundation of Henan Province(262300421690); Basic Research Project of Henan Provincial Key Scientific Research Project(26ZX009)

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Abstract

The electrochemical construction of C—S bonds enables the efficient synthesis of β,β-dialkoxy thioethers from terminal alkynes, thiophenols, and alcohols. This method eliminates the need for stoichiometric oxidants and metal catalysts. By employing an electrochemical platform to provide a stable current, two platinum electrodes were utilized as the anode and cathode in an electrolytic cell, with lithium perchlorate as the electrolyte and acetonitrile as the solvent. Under room temperature and pressure, electrolysis was conducted at a constant current of 12 mA for 5 h, affording the targeted thioether compound in good yield. Mechanistic studies revealed that the reaction involves anodic oxidation to generate radical cation intermediates, formation of a three-membered cyclic intermediate, and radical oxidative coupling processes. This strategy demonstrates excellent compatibility with diverse functional groups, offering a green and sustainable alternative for C—S bond formation.

Key words: electrosynthesis, terminal alkynes, β, β-dialkoxy sulfides

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Wensheng Zhang, Jianhang Zhang, Jianming Liu, Qinghu Tang. Electrochemical Three-Component Synthesis of β,β-Dialkoxy Sulfides from Terminal Alkynes, Thiophenols, and Alcohols[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2399-2408.

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Fig. & Tab. 9

Scheme 1. Electrochemical three-component synthesis of β,β-dialkoxy sulfides from terminal alkynes, thiophenols and alcohols

Entry	Variation from the standard conditions	Yield^b/%

Table 1. Optimization of reaction conditions

Table 2. Scope of substrates of 4-chlorothiophenol and phenylacetylene derivatives

Table 3. Scope of phenylacetylene and thiophenol derivatives

Scheme 2. Gram-synthesis

Scheme 3. Control experiment

Figure 1. Cyclic voltammetry

Scheme 4. Proposed mechanism

Scheme 5. Electrochemical three-component synthesis of β,β- dialkoxy sulfides from terminal alkynes, thiophenols and alcohols

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电化学促进芳香炔、芳基硫酚和醇三组分合成β,β-二烷氧基硫醚

Electrochemical Three-Component Synthesis of β,β-Dialkoxy Sulfides from Terminal Alkynes, Thiophenols, and Alcohols

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