Syntheses of α-monofluoroalkyl acetophenones from fluoroalkyl carboxylic NHPI esters and silyl enol ethers by photocatalytic decarboxylative reaction

•α-monofluoroalkyl carboxylic NHPI Esters were employed as α-monofluoroalkylation radical reagents.•A series of α-monofluoroalkyl acetophenones were produced via photoredox-catalyzed decarboxylative α-monofluoroalkylation of silyl enol ethers in modest to good yields.•The method was applied to synth...

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Veröffentlicht in:Journal of fluorine chemistry 2024-05, Vol.276, p.110279, Article 110279
Hauptverfasser: Kou, Min, Zheng, Jianli, Chen, Tong, Wu, Yanghao, Huang, Ling, Cao, Dongdong, Chen, Dingben
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Sprache:eng
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Zusammenfassung:•α-monofluoroalkyl carboxylic NHPI Esters were employed as α-monofluoroalkylation radical reagents.•A series of α-monofluoroalkyl acetophenones were produced via photoredox-catalyzed decarboxylative α-monofluoroalkylation of silyl enol ethers in modest to good yields.•The method was applied to synthesize antalgic activity compound containing α-monofluoroalkyl acetophenone skeleton. A photoredox-catalyzed decarboxylative α-monofluoroalkylation of silyl enol ethers with fluoroalkyl carboxylic N-(hydroxy)phthalimide esters has been successfully developed. Diverse functionalized α-monofluoroalkyl acetophenones were produced in modest to good yields under mild and operationally simple conditions. The developed method was further applied to synthesize antalgic and ataractic activity compound containing α-monofluoroalkyl acetophenone skeleton. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2024.110279