Progresses on Fluorocarbon-Containing Substrates Involved Carbonylation Reactions

doi:10.6023/cjoc202301010

Abstract

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

Cite this article

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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Fig. & Tab. 28

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

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

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

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

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

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

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

Scheme 8. Palladium-catalyzed carbonylation of alkenes and ArIF2

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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