Nucleophilic difluoroalkylation of benzophenones, benzaldehydes and Schiff's bases by tetrafluoroethyl ether and difluoroacetamide

• CH functionalization of gem difluoromethyl group..
• Formation of new type of fluorine containing alcohols and amines.
• Unusual role of solvent in modifying the course of the reaction.

From gem-difluoromethyl group of 1,1,2,2-tetrafluoroethyl ether and 2,2-difluoroalkylamide, proton can be removed by potassium bis(trimethylsilyl)amide in DMF, THF or toluene. The generated nucleophiles are then condensed with benzophenones, benzaldehydes or Schiff's bases to provide new fluorinated alcohols and amines. Some interesting solvent effects are also observed.

Figure optionsDownload as PowerPoint slide