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Keywords:

  • C[BOND]O bond formation;
  • enolates;
  • fluorine;
  • O-alkylation;
  • regioselectivity
Thumbnail image of graphical abstract

Expect the unexpected: The self-stable salts 1, X=OTf, PF6, x=2, y=1, developed for electrophilic monofluoromethylation showed inherent selectivity for the O-alkylation of enolates, thus providing access to monofluoromethyl ethers, which are difficult to obtain by the direct electrophilic fluoromethylation of alcohols. Salt 1, X=BF4, x=0, y=3, in contrast leads to C-alkylated products.