Recent Advances in Electrochemical Silylation

doi:10.6023/cjoc202308022

Abstract

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

Cite this article

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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Fig. & Tab. 17

Scheme 1. Electrochemical silylation reactions

Scheme 2. Cathodic reduction of chlorosilanes

Scheme 3. Electroreductive coupling of chlorosilanes

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

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

Scheme 6. Mechanistic studies for the electroreductive activation of chlorosilanes

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

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

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

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

Scheme 11. Electrochemical silyl-oxygenation of alkenes

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

Scheme 13. Electrochemical silylation reactions using NHPI as HAT catalyst

Scheme 14. Electrophotocatalytic Si—H activation

Scheme 15. Electrophotocatalytic C—H silylation of heteroarenes

Scheme 16. Electrochemical hydrosilylation of alkynes

Scheme 17. Electrochemical synthesis of fluorinated allyl silanes

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