电化学硅基化反应的研究进展

doi:10.6023/cjoc202308022

摘要/Abstract

有机硅化合物因其独特的物理化学性质, 被广泛应用于合成、材料及医药等领域, 受到了化学家们的广泛关注. 因此, 发展温和高效的合成方法构建有机硅化合物显得尤为重要. 近年来, 有机电化学得到了快速的发展, 为合成有机硅化合物提供了一种全新的策略. 其条件绿色温和、反应简单高效以及无需额外氧化还原试剂等优点, 使得通过电化学硅基化反应合成有机硅化合物取得了长足的发展. 根据硅前体和电化学反应类型的不同, 主要从阴极还原硅基化反应和阳极氧化硅基化反应两个方面综述了电化学硅基化反应的研究进展.

关键词: 电化学, 硅基化反应, 有机硅, 阴极还原, 阳极氧化

Organosilicon compounds are widely applied in synthesis, materials, medicine and other fields due to their unique physical and chemical properties, and have attracted widespread attention from chemists. Therefore, it is particularly important to develop mild and efficient synthesis methods to construct organosilicon compounds. In recent years, the rapid development of electrochemistry provided a new strategy for the synthesis of organosilicon compounds. Due to its advantages of green and mild conditions, simple and efficient reactions, and no need for additional redox reagents, significant progress has been made in the synthesis of organosilicon compounds through electrochemical silylation reactions. The latest progress in electro- chemical silylation is mainly reviewed from two aspects: electrochemical silylation reactions via cathodic reduction, and electrochemical silylation reactions via anodic oxidation.

Key words: electrochemistry, silylation, organosilicon, cathodic reduction, anodic oxidation

引用此文

王竣永, 李娜, 柯杰, 何川. 电化学硅基化反应的研究进展[J]. 有机化学, 2024, 44(3): 927-939.

Junyong Wang, Na Li, Jie Ke, Chuan He. Recent Advances in Electrochemical Silylation[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 927-939.

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图/表 17

图式1. 电化学硅基化反应

Scheme 1. Electrochemical silylation reactions

图式2. 氯硅烷的阴极还原

Scheme 2. Cathodic reduction of chlorosilanes

图式3. 氯硅烷的电化学还原偶联反应

Scheme 3. Electroreductive coupling of chlorosilanes

图式4. 氯硅烷的电化学还原策略合成二硅烷和低聚硅烷

Scheme 4. Electroreductive strategy to synthesize disilanes and oligosilanes from chlorosilanes

图式5. 氯硅烷的电化学还原策略合成邻二硅烷和环硅烷

Scheme 5. Electroreductive strategy to synthesize vicinal disilane and silacycle from chlorosilanes

图式6. 氯硅烷电化学还原活化的机理研究

Scheme 6. Mechanistic studies for the electroreductive activation of chlorosilanes

图式7. 镍催化烯炔与氯硅烷和烷基溴代物之间的电还原偶联反应

Scheme 7. Nickel-catalyzed electroreductive cross-coupling of enynes with chlorosilanes and alkyl bromides

图式8. 镍催化的三组分电还原偶联反应的机理研究

Scheme 8. Mechanistic studies for the nickel-catalyzed three-component electroreductive cross-coupling

图式9. 阳极氧化产生硅自由基的三种途径

Scheme 9. Three pathways for generating silyl radical through anodic oxidation

图式10. 氢硅烷电化学水解或醇解合成硅醇或硅醚

Scheme 10. Electrochemical hydrolysis and alcoholysis of hydrosilanes to silanols and silyl ethers

图式11. 电化学促进烯烃的硅氧化反应

Scheme 11. Electrochemical silyl-oxygenation of alkenes

图式12. 电化学促进烯烃的硅氧化反应的机理研究

Scheme 12. Mechanistic studies for the electrochemical silyl-oxygenation of alkenes

图式13. NHPI作为氢原子转移催化剂的电化学硅基化反应

Scheme 13. Electrochemical silylation reactions using NHPI as HAT catalyst

图式14. 光电共催化的Si—H键活化

Scheme 14. Electrophotocatalytic Si—H activation

图式15. 光电共催化的杂芳烃C—H硅基化反应

Scheme 15. Electrophotocatalytic C—H silylation of heteroarenes

图式16. 电化学炔烃的氢硅化反应

Scheme 16. Electrochemical hydrosilylation of alkynes

图式17. 电化学合成氟化烯丙基硅烷

Scheme 17. Electrochemical synthesis of fluorinated allyl silanes

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