可见光催化有机硅的合成研究进展

doi:10.6023/cjoc202306028

摘要/Abstract

硅杂化合物广泛存在于药物分子和具有特殊用途的功能材料中. 与其同主族的全碳母体化合物相比, 通常硅元素的存在赋予了相应的硅杂化合物特殊的生物活性和独特的物理化学性能. 概述了近年来可见光催化有机硅的合成方法和策略, 并对其反应机理和局限性予以分析和讨论.

关键词: 可见光催化, 硅基自由基, 氢硅基化, 硅碳化, 脱氟硅基化

Silahydrocarbons are often encountered in pharmaceuticals and material chemistry. In comparison with all-carbon parent compounds, carbon/silicon switch generally endows the corresponding compounds with different biological activity and physical-chemical properties. In this review, the methods and strategies of synthesis of organosilanes by photoredox in recent years are reviewed, and the corresponding reaction mechanisms and limitations are discussed.

Key words: photocatalysis, silicon radical, hydrosilylation, silacarboxylation, defluorosilylation

引用此文

陈凤娟, 刘罗, 张子露, 曾伟. 可见光催化有机硅的合成研究进展[J]. 有机化学, 2023, 43(10): 3454-3469.

Fengjuan Chen, Luo Liu, Zilu Zhang, Wei Zeng. Recent Progress in Synthesis of Organosilanes Driven by Visible-Light[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3454-3469.

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图/表 22

图式1. 光氧化还原产生硅基自由基

Scheme 1. Photochemical generation of silyl radicals

图式2. TBADT-光催化缺电子烯烃的氢硅基化

Scheme 2. TBADT-photocatalyzed hydrosilylation of electron-poor olefins

图式3. 可见光介导无金属催化烯烃的氢硅基化

Scheme 3. Visible-light-mediated metal-free hydrosilylation of alkenes

图式4. 可见光介导中性或富电子烯烃的反式硅氢化

Scheme 4. Visible light-driven radical trans-hydrosilylation of electron-neutral and -rich alkenes

图式5. 可见光驱动单/双取代联烯的自由基氢硅化反应

Scheme 5. Access to functionalized E-allylsilanes and E-alkenylsilanes through visible-light-driven radical hydrosilylation of mono- and disubstituted allenes

图式6. 可见光催化硅基自由基经1,6-共轭加成合成二芳基甲基硅烷

Scheme 6. Photocatalytic synthesis of diarylmethyl silanes via 1,6-conjugate addition of silyl radicals

图式7. 可见光介导杂1,6-二烯的硅基化环化反应

Scheme 7. Visible-light-driven silylative cyclization of aza-1,6-dienes

图式8. 可见光介导烯炔和二烯的氢硅基化和氢膦化/环化反应

Scheme 8. Visible-light mediated hydrosilylative and hydrophosphorylative cyclizations of enynes and dienes

图式9. 可见光介导无金属参与烯烃的硅羧基化或碳羧基化

Scheme 9. Visible-light-mediated metal-free silacarboxylation or carbocarboxylation of alkenes

图式10. 光氧化还原/氢原子转移/钴催化协同助力烯烃的脱氢硅基化反应

Scheme 10. Dehydrogenative silylation of alkenes for the synthesis of substituted allylsilanes by photoredox, hydrogen-atom transfer, and Cobalt catalysis

图式11. 可见光介导烯烃的硅碳化反应

Scheme 11. Visible-light-mediated silacarboxylation of alkenes

图式12. 可见光介导三氟甲基芳基烯烃的脱氟硅基化

Scheme 12. Light-mediated defluorosilylation of trifluoromethyl arylalkenes

图式13. 可见光介导炔烃的自由基氢硅基化

Scheme 13. Light-mediated radical hydrosilylation of alkynes

图式14. 可见光催化杂芳烃的C—H硅基化

Scheme 14. Photocatalytic C—H silylation of heteroarenes by using trialkylhydrosilanes

图式15. 可见光催化杂芳烃和芳烃的硅基化

Scheme 15. Photoinduced silylation of heteroarenes or arenes

图式16. 可见光介导硅基化反应

Scheme 16. Visible-light-mediated silylation reactions

图式17. 可见光介导Si—Si试剂产生硅基自由基

Scheme 17. Photo-mediated silyl radicals from Si—Si reagents

图式18. 可见光诱导硅硼试剂产生硅基自由基

Scheme 18. Photo-generated silyl radicals from Si—B reagents

图式19. 有机光氧化还原催化硅基硼酸盐产生硅基自由基

Scheme 19. Organic photoredox-catalyzed silyl radical generation from silylboronate

图式20. 可见光诱导硅基羧酸产生硅基自由基

Scheme 20. Photo-generated silyl radicals from silacarboxylic acids

图式21. 光催化烯基硅烷和芳烃磺酰基叠氮的环芳构化

Scheme 21. Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides

图式22. 光催化硅杂烯炔和硫代磺酸酯的硫磺酰化反应

Scheme 22. Photocatalyzed thiosulfonylation of sila-enynes with thiosulfonates

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