Fluoride-catalyzed Nucleophilic Addition of PhSCF2SiMe3 to Isatins: Synthesis of 3-(1',1'-Difluoroalkyl)-3-hydroxyindolin-2-ones
作者： Sirisuk Keereewan , Darunee Soorukram , Chutima Kuhakarn , Vichai Reutrakul , Manat Pohmakotr
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摘要: Synthesis of 3-(1',1'-difluoroalkyl)-3-hydroxyindolin-2-ones employing α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) as a gem-difluoromethylene building block is described. The reaction entailed fluoride-catalyzed nucleophilic addition PhSCF2SiMe3 to isatin derivatives followed by reductive cleavage phenylsulfanyl group leading 3-(difluoromethyl)-3-hydroxyindolin-2-ones in good yields. Under similar reduction conditions, the presence activated olefins, an intermolecular radical trapping reactions took place yield 3-(1',1'-difluoroalkyl)-3-hydroxyindolin-2-ones.
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