硫代磺酸酯的合成与应用研究进展

doi:10.6023/cjoc202203036

有机化学 ›› 2022, Vol. 42 ›› Issue (8): 2322-2330.DOI: 10.6023/cjoc202203036 上一篇下一篇

综述与进展

硫代磺酸酯的合成与应用研究进展

宇世伟, 陈兆华, 陈淇, 林舒婷, 何金萍, 陶冠燊, 汪朝阳^*()

华南师范大学化学学院教育部环境理论化学重点实验室广州市生物医学分析化学重点实验室 GDMPA手性药物过程控制与质量评价重点实验室广州 510006

收稿日期:2022-03-18 修回日期:2022-04-21 发布日期:2022-05-26
通讯作者: 汪朝阳
基金资助:
广东省基础与应用基础研究基金(2021A1515012342); 广东省科技计划(2017A010103016); 华南师范大学专项人才培养计划([2021]72); 广东省质量工程建设项目专项人才培养计划资助项目([2021]29)

Research Progress in Synthesis and Application of Thiosulfonates

Shiwei Yu, Zhaohua Chen, Qi Chen, Shuting Lin, Jinping He, Guanshen Tao, Zhaoyang Wang()

GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals;Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine;Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education;School of Chemistry, South China Normal University, Guangzhou 510006

Received:2022-03-18 Revised:2022-04-21 Published:2022-05-26
Contact: Zhaoyang Wang
Supported by:
Guangdong Basic and Applied Basic Research Foundation(2021A1515012342); Guangdong Provincial Science and Technology Project(2017A010103016); Special Talent Training Program of South China Normal University([2021]72); Guangdong Province Quality Engineering Construction Project for Special Talent Training Plan([2021]29)

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摘要/Abstract

硫代磺酸酯是一种重要的合成子, 可与炔、烯、醛以及卤代烃等化合物反应, 得到硫醚、砜类等硫化物. 同时, 硫代磺酸酯还具备抗病毒、抗真菌等作用, 其制备与在有机合成中的应用备受人们关注. 鉴于此, 以催化剂种类与绿色化学新进展为依据, 总结了常见的硫代磺酸酯的合成策略; 同时, 以反应物种类及其反应类型为依据, 综述了近年来它们在有机合成中的应用. 展望未来, 在基于硫代磺酸酯构建新硫化物的反应研究中, 双官能团化反应具有较好的研究前景.

关键词: 硫代磺酸酯, 绿色化学, C—S键构建, 光催化, 自由基反应, 双官能团化反应

As an important kind of synthons, thiosulfonates can react with alkynes, alkenes, aldehydes, and halogenated hydrocarbons to synthesize thioethers and sulfones. At the same time, some thiosulfonate compounds have anti-viral and anti-fungal bioactivities. The synthesis of thiosulfonates and their applications in organic synthesis have been under the spotlight. Thus, according to different types of catalysts and new progress in green chemistry, the synthesis progress of thiosulfonates is summarized. On the other hand, according to the types of reactants and reaction types, the application progress of thiosulfonates in organic synthesis is reviewed. In the future, among the researches on the construction of new sulfides with thiosulfonates, various difunctionalization reactions are still promising directions.

Key words: thiosulfonate, green chemistry, C—S bond formation, photocatalysis, radical reaction, difunctionalization reaction

引用此文

宇世伟, 陈兆华, 陈淇, 林舒婷, 何金萍, 陶冠燊, 汪朝阳. 硫代磺酸酯的合成与应用研究进展[J]. 有机化学, 2022, 42(8): 2322-2330.

Shiwei Yu, Zhaohua Chen, Qi Chen, Shuting Lin, Jinping He, Guanshen Tao, Zhaoyang Wang. Research Progress in Synthesis and Application of Thiosulfonates[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2322-2330.

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图/表 8

图式1. 磺酰氯在不同的铜盐/配体/还原剂体系中合成硫代磺酸酯类化合物

Scheme 1. Synthesis of thiosulfonate compounds from sulfonyl chlorides in different copper salt/ligand/reductant systems

图式2. 亚磺酰胺生成对称和不对称硫代磺酸酯类化合物的合成反应

Scheme 2. Synthesis reaction of symmetrical/unsymmetrical thiosulfonate compounds from sulfinamides

图式3. 亚磺酸钠在BF3•OEt2介导下生成“对称”和“不对称”的硫代磺酸酯类化合物

Scheme 3. Synthesis of symmetrical/unsymmetrical thiosulfonate compounds from sodium sulfinates mediated by BF3•OEt2

图式4. 磺酰氯生成三氟甲基硫代磺酸酯的合成反应

Scheme 4. Synthesis reaction of trifluoromethyl thiosulfonate compounds from sulfonyl chlorides

图式5. 磺酰氯在四丁基碘化铵介导下生成硫代磺酸酯与二硫化物

Scheme 5. Synthesis of thiosulfonates and disulfides from sulfonyl chlorides mediated by tetrabutylammonium iodide

图式6. 炔与硫代磺酸酯合成乙烯基砜类化合物

Scheme 6. Synthesis of vinyl sulfones compounds from thiosulfonate and alkyne

图式7. 铜催化下炔与叠氮基硫代磺酸酯合成5-硫代三唑类化合物的串联反应

Scheme 7. Copper(I)-catalyzed tandem reaction of 5-thio triazoles compounds from alkyne and azidothiosulfonate

图式8. 可见光促进下芳基重氮盐与S-氘代甲基硫代磺酸酯交叉偶联反应

Scheme 8. Visible-light promoted cross-coupling reactions of aryldiazonium salts and S-methyl-d3 thiosulfonate

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硫代磺酸酯的合成与应用研究进展

Research Progress in Synthesis and Application of Thiosulfonates

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