含碳氟类底物参与的羰基化反应研究进展

doi:10.6023/cjoc202301010

摘要/Abstract

含氟有机分子的合成和转化已蓬勃发展成为氟化学重要的前沿课题之一, 它深刻地影响着生命科学和材料科学. 其中碳氟化合物参与的羰基化反应是近几年发展起来的一类羰基化反应, 它拥有诸多的挑战. 介绍了过渡金属钯、镍和铜催化的碳氟化合物参与的羰基化反应研究进展. 为了理解这些反应的历程, 也选择了一些具有代表性的反应介绍其反应机理.

关键词: 碳氟化合物, 羰基化反应

The synthesis and transformation of fluorine-containing organic molecules has experienced vigorously development and has become one of the most important frontier topics of fluorine chemistry, which profoundly affects life science and material science. Among them, carbonylative transformation of fluorocarbon-containing substrates is a carbonylation reaction developed in recent years which still has many challenges. This review summarized the progresses on fluorocarbon-containing substrates carbonylation reactions based on transition metal palladium, nickel and copper catalysis. In order to understand the mechanism of these reactions, representative reactions were selected for detailed discussion.

Key words: fluorocarbon, carbonylation reaction

引用此文

安大列, 包志鹏, 吴小锋. 含碳氟类底物参与的羰基化反应研究进展[J]. 有机化学, 2023, 43(7): 2304-2312.

Da-Lie An, Zhi-Peng Bao, Xiao-Feng Wu. Progresses on Fluorocarbon-Containing Substrates Involved Carbonylation Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2304-2312.

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图/表 28

图式1. 钯催化苯硼酸和二氟酰胺\酯的羰基化反应

Scheme 1. Palladium-catalyzed carbonylation of phenylboronic acid and difluoroamide/ester

图式2. 钯催化烷基-9-BBN与二氟化合物的羰基化反应

Scheme 2. Palladium-catalyzed carbonylation reaction of alkyl- 9-BBN with difluoro compounds

图式3. 钯催化烷基-9-BBN与二氟化合物的羰基化反应机理

Scheme 3. Palladium-catalyzed carbonylation reaction mechanism of alkyl-9-BBN with difluoro compounds

图式4. 钯催化炔烃、二氟酯和亲核试剂的羰基化反应

Scheme 4. Palladium-catalyzed carbonylation of alkynes, di- fluoroesters and nucleophiles

图式5. 钯催化炔烃、二氟酯和亲核试剂的羰基化反应机理

Scheme 5. Palladium-catalyzed carbonylation reaction mechanism of alkynes, difluoroesters and nucleophiles

图式6. 钯催化烯烃和二氟化合物的羰基化反应

Scheme 6. Palladium-catalyzed carbonylation of alkenes and difluoro compounds

图式7. 钯催化烯烃和二氟化合物的羰基化反应机理

Scheme 7. Mechanism for Palladium-catalyzed carbonylation of alkenes and difluoro compounds

图式8. 钯催化烯烃和ArIF2的羰基化反应

Scheme 8. Palladium-catalyzed carbonylation of alkenes and ArIF2

图式9. 钯催化烯烃、ArIF2和亲核试剂的羰基化反应机理

Scheme 9. Palladium-catalyzed carbonylation reaction mechanism of alkenes, ArIF2 and nucleophiles

图式10. 钯催化烯烃和全氟烷烃和亲核试剂的羰基化反应

Scheme 10. Palladium-catalyzed carbonylation of alkenes and perfluoroalkanes with nucleophiles

图式11. 钯催化烯烃和全氟烷烃和亲核试剂的羰基化反应机理

Scheme 11. Palladium-catalyzed carbonylation reaction mechanism of alkenes and perfluoroalkanes with nucleophiles

图式12. 钯催化2-烯丙基芳基三氟甲磺酸酯的羰基化反应

Scheme 12. Palladium-catalyzed carbonylation of 2-allylaryl tri- flate

图式13. 钯催化偕二氟烯烃氢化的羰基化反应

Scheme 13. Palladium-catalyzed carbonylation reaction for hydrogenation of gem-difluoroalkenes

图式14. 钯催化偕二氟烯烃脱氟的羰基化反应

Scheme 14. Palladium-catalyzed carbonylation reaction for defluorination of gem-difluoroalkenes

图式15. 钯催化偕二氟烯烃脱氟的羰基化反应机理

Scheme 15. Palladium-catalyzed carbonylation reaction mechanism for defluorination of gem-difluoroalkenes

图式16. 钯催化氟化烯烃和苯胺的羰基化反应

Scheme 16. Palladium-catalyzed carbonylation of fluorinated alkenes and anilines

图式17. 钯催化氟化烯烃和苯胺的羰基化反应机理

Scheme 17. Palladium-catalyzed carbonylation reaction mechanism of fluorinated alkenes and anilines

图式18. 钯催化二氟卡宾的可控性转化

Scheme 18. Palladium-catalyzed controllable conversion of di- fluorocarbene

图式19. 钯催化二氟卡宾的可控性转化机理

Scheme 19. Palladium-catalyzed controllable conversion me- chanism of difluorocarbene

图式20. 镍催化芳基苯硼酸与二氟烷基溴的羰基化反应

Scheme 20. Nickel-catalyzed carbonylation of arylphenylboronic acid with difluoroalkyl bromide

图式21. 镍催化芳基苯硼酸与二氟烷基溴的羰基化反应机理

Scheme 21. Nickel-catalyzed carbonylation reaction mechanism of arylphenylboronic acid and difluoroalkyl bromide

图式22. 镍催化烯烃与二氟烷基溴的羰基化反应

Scheme 22. Nickel-catalyzed carbonylation of alkenes with difluoroalkyl bromides

图式23. 镍催化仲烷基卤代物与芳基苯硼酸的羰基化反应

Scheme 23. Nickel-catalyzed carbonylation of secondary alkyl halides with arylphenylboronic acids

图式24. 镍催化3-溴-3,3-二氟丙烯与芳基苯硼酸的羰基化反应

Scheme 24. Nickel-catalyzed carbonylation of 3-bromo-3,3- difluoropropene with arylphenylboronic acid

图式25. 镍催化3-溴-3,3-二氟丙烯与芳基苯硼酸的羰基化反应的机理

Scheme 25. Mechanism of nickel-catalyzed carbonylation of 3-bromo-3,3-difluoropropene with arylphenylboronic acid

图式26. 铜催化烯烃、Togni-II试剂与胺的羰基化反应

Scheme 26. Copper-catalyzed carbonylation of alkenes, Togni-II reagents and amines

图式27. 铜催化烯烃、Togni-II试剂与胺的羰基化反应机理

Scheme 27. Copper-catalyzed carbonylation reaction mechanism of alkenes, Togni-II reagents and amines

图式28. 铜催化烯烃与全氟烷基碘的羰基化反应

Scheme 28. Copper-catalyzed carbonylation of alkenes with perfluoroalkyl iodides

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