Fluoride-catalyzed Nucleophilic Addition of PhSCF2SiMe3 to Isatins: Synthesis of 3-(1',1'-Difluoroalkyl)-3-hydroxyindolin-2-ones

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 of PhSCF2SiMe3 to isatin derivatives followed by reductive cleavage of a phenylsulfanyl group leading to 3-(difluoromethyl)-3-hydroxyindolin-2-ones in good yields. Under similar reduction conditions, in the presence of activated olefins, an intermolecular radical trapping reactions took place to yield 3-(1',1'-difluoroalkyl)-3-hydroxyindolin-2-ones.

from # All Medicine by Alexandros G. Sfakianakis via alkiviadis.1961 on Inoreader http://ift.tt/2fL8v0w