芳烃与烷烃化合物参与的光化学与电化学硼化反应

doi:10.6023/cjoc202212041

摘要/Abstract

有机硼化合物是重要的有机合成砌块, 并被广泛应用于材料与医药领域. 发展实用、简洁的硼化反应合成有机硼化合物一直是有机硼化学的核心课题之一. 近年来, 光化学和电化学硼化反应取得了快速发展, 已成为合成有机硼化合物的重要方法. 从能量来源及反应底物类型的角度出发, 总结了芳烃与烷烃化合物参与的光化学、电化学和光电化学硼化反应的研究进展, 同时也对今后光化学与电化学硼化反应的发展方向进行了展望.

关键词: 光化学, 电化学, 光电化学, 硼化反应, 有机硼化合物

Organoboron compounds are important building blocks in organic synthesis and have been widely applied in materials and pharmaceutical science. The development of practical and concise borylation reactions to synthesize organoboron compounds has always been one of the core topics of organoboron chemistry. Recently, photochemical and electrochemical borylation reactions have gained rapid development and emerged as important methods towards the synthesis of organoboron compounds. The recent research progress concerning photochemical, electrochemical and photoelectrochemical borylation involving aryl and alkyl compounds from the view of energy resources and substrates is reviewed. Additionally, research trends of this area are also discussed.

Key words: photochemistry, electrochemistry, photoelectrochemistry, borylation, organoboron compound

引用此文

杜琳琳, 张华. 芳烃与烷烃化合物参与的光化学与电化学硼化反应[J]. 有机化学, 2023, 43(5): 1726-1741.

Linlin Du, Hua Zhang. Photochemical and Electrochemical Borylation Involving Aryl and Alkyl Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1726-1741.

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图/表 24

图式1. 有机硼化合物的应用

Scheme 1. Applications of organoboron compounds

图式2. 光氧化还原催化和电合成

Scheme 2. Photoredox catalysis and electrosynthesis

图式3. 光化学与电化学硼化反应

Scheme 3. Photochemical and electrochemical borylation

图式4. 溴代芳烃和碘代芳烃的光化学硼化反应

Scheme 4. Photochemical borylation of aryl bromides and iodides

图式5. 氯代芳烃的光化学硼化反应

Scheme 5. Photochemical borylation of aryl chlorides

图式6. 氟代芳烃的光化学硼化反应

Scheme 6. Photochemical borylation of aryl fluorides

图式7. 卤代烷烃的光化学硼化反应

Scheme 7. Photochemical borylation of alkyl halides

图式8. 芳基重氮盐和芳基偶氮砜的光化学硼化反应

Scheme 8. Photochemical borylation of aryldiazonium salts and arylazo sulfones

图式9. 烷基吡啶盐的光化学硼化反应

Scheme 9. Photochemical borylation of alkyl pyridinium salts

图式10. 芳基季铵盐的光化学硼化反应

Scheme 10. Photochemical borylation of aryl quaternary ammonium salts

图式11. 芳胺的光化学硼化反应

Scheme 11. Photochemical borylation of anilines

图式12. 芳基肼盐酸盐的光化学硼化反应

Scheme 12. Photochemical borylation of arylhydrazine hydrochlorides

图式13. N-羟基邻苯二甲酰亚胺酯的光化学脱酸硼化反应

Scheme 13. Photochemical borylation of N-hydroxyphthalimide esters

图式14. 醇类或酚类衍生物的光化学硼化反应

Scheme 14. Photochemical borylation of alcohol and phenol derivatives

图式15. 烷基和芳基硫化物的光化学硼化反应

Scheme 15. Photochemical borylation of alkyl and aryl sulfides

图式16. 烷烃的光化学硼化反应

Scheme 16. Photochemical borylation of alkanes

图式17. 氮杂芳环的光化学硼化反应

Scheme 17. Photochemical borylation of azines

图式18. 卤代物的电化学硼化反应

Scheme 18. Electrochemical borylation of halides

图式19. 芳基和苄基季铵盐的电化学硼化反应

Scheme 19. Electrochemical borylation of alkyl and benzyl quaternary ammonium salts

图式20. 烷基N-羟基邻苯二甲酰亚胺酯的电化学硼化反应

Scheme 20. Electrochemical borylation of alkyl N-hydroxy- phthalimide esters

图式21. 芳基偶氮砜的电化学硼化反应

Scheme 21. Electrochemical borylation of arylazo sulfones

图式22. 芳基肼盐酸盐的电化学硼化反应

Scheme 22. Electrochemical borylation of arylhydrazine hydrochlorides

图式23. 硝基芳烃的电化学硼化反应

Scheme 23. Electrochemical borylation of nitroarenes

图式24. 氯代芳烃和碘代芳烃的电光催化硼化反应

Scheme 24. Electrophotocatalytic borylation of aryl chlorides and bromides

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