Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones

doi:10.6023/cjoc202304025

Abstract

Acyl-Ni has emerged as an important synthetic intermediate in organic synthesis. In recent years, a strategy for the synthesis of ketones with acyl-Ni species as a key intermediate for synthesizing ketones has attracted broad attention. Compared with the traditional cross-coupling involving organometallic reagents, reductive acylation using the in situ generated acyl-Ni species with various carbon electrophiles exhibits many notable advantages, such as mild conditions, high step economy, widely functional group tolerance, and environmentally friendly. This review focuses on the recent advances in Ni-catalyzed reductive acylation of various carbon electrophiles with a broad range of carboxylic acids or carboxylic acid derivatives.

Key words: acyl nickel, reductive acylation, nickel catalysis, ketones, electrophiles

Cite this article

Yunpeng Qi, Dengkai Lin, Liang-An Chen. Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3861-3875.

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Fig. & Tab. 27

Scheme 1. Synthesis of ketones by reductive acylation reactions via acyl nickel intermediates

Scheme 2. Reductive acylation of acyl chlorides and alkyl iodides

Scheme 3. Three-component reductive acylation of unactivate olefins, perfluoroalkyl iodides and acyl chlorides

Scheme 4. Reductive acylation of acyl fluorides and alkenyl trifluoromethanesulfonates

Scheme 5. Reductive acylation of acyl halides and N-alkyl pyridinium salts

Scheme 6. Asymmetric reductive acylation of alkyl chlorides and acyl chlorides

Scheme7 Asymm. etric reductive acylation of acyl chlorides and α-trifluoroalkyl bromides Asymmetric reductive acylation of acyl chlorides and α-trifluoroalkyl bromides

Scheme 8. Asymmetric reductive acylation of acyl chlorides and α-bromobenzoates

Scheme 9. Reductive acylation of carboxylic acids with tertiary alkyl or glycosyl halides

Scheme 10. Decarboxylative reductive acylation of amides and carboxylic acids

Scheme 11. Migratory reductive acylation of alkyl halides and carboxylic acids

Scheme 12. Light-promoted Ni-catalyzed decarboxylative reductive acylation of carboxylic acids

Scheme 13. Migratory reductive acylation of carboxylic acids with olefins or alkyl halides

Scheme 14. Reductive acylation of amides

Scheme 15. Reductive acylation of acylimidazoles with alkyl bromides or aryl bromides

Scheme 16. Reductive acylation of amides and alkyl bromides

Scheme 17. Nickel/Zirconium catalyzed reductive acylation of alkyl iodides and pyridine thioesters

Scheme 18. Light-promoted Ni-catalyzed decarboxylative reductive acylation of carboxylic acids and thioesters

Scheme 19. Reductive acylation of phenolic esters and alkyl bromides

Scheme 20. Light-promoted Ni-catalyzed reductive acylation of pyridyl esters and NHPI esters

Scheme 21. Reduction acylation reaction of diphenyl oxalate with alkyl bromide or alkyl p-toluenesulfonate

Scheme 22. Three-component reductive acylation of alkyl halides, olefins and chloroformates

Scheme 23. Three-component reductive acylation of alkyl halides and chloroformates

Scheme 24. Three-component reductive acylation of aryl halides, alkyl halides and chlorofomates

Scheme 25. Three-component reductive hydrocarbonylation of alkenes

Scheme 26. Reductive acylation of alkyl halides and chloroformates

Scheme 27. Reductive acylation of aryl triflates and thiocarbo- nates

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