期刊
ACS CATALYSIS
卷 9, 期 7, 页码 6555-6563出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b01312
关键词
photoredox catalysis; difluoromethylation; alkene difunctionalization; radical reaction; flow synthesis
资金
- JSPS (KAKENHI) [22350026, JP16H06038, JP18H04241]
- Naito Foundation
- JST CREST [JPMJCR18R4]
A step-economical method for synthesis of alpha-CF2H-substituted ketones from readily available alkene feed-stocks has been developed. Radical difluoromethylation of aromatic alkenes combining DMSO oxidation and photoredox catalysis is a key to the successful transformation. Electrochemical analysis, laser flash photolysis (LFP), and density functional theory (DFT) calculations reveal that N-tosyl-S-difluoromethyl-S-phenylsulfoximine serves as the best CF2H radical source among analogous sulfone-based CF2H reagents. The present photocatalytic keto-difluoromethylation has been applied to flow synthesis and easily scaled up to gram-scale synthesis within a reasonable reaction time, Furthermore, potentials of the alpha-CF2H-substituted ketones for useful synthetic intermediates are shown; e.g., synthesis of the CF2H-containing alpha-hydroxyamide with the same carbon skeleton as that of the anticonvulsant active CF3-analogue, is disclosed. Additionally, mechanistic studies are also discussed in detail.
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