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Keywords:

  • C-alkylation;
  • enolates;
  • fluoromethylation;
  • O-alkylation;
  • regioselectivity
Thumbnail image of graphical abstract

Fluoromethylation. The C/O regioselectivity of β-ketoesters with fluorinated methylsulfoxinium salts 2 is discussed. Trifluoromethylation involves the formation of a more cationic species represented by +CF3 to provide C-alkylated products, while monofluoromethylation possibly proceeds involving a more radical-like species such as .CFH2 to give O-alkylated species. Difluoromethylation could involve both cationic and radical species, which afford a mixture of C and O isomers.