Selective ortho-arylation of polyfluorinated hydroxyaromatic compounds with lead aryl acetates

Article abstract of DOI:10.1016/S0022-1139(00)80568-0

Reactions of salts of pentafluorophenol and heptafluoronaphthols with lead aryl acetates have led to the formation of arylcyclohexadienones with an ortho-quinoid structure.The arylation of sodium pentafluorophenoxide and heptafluoro-2-naphthoxide is accompanied by nucleophilic substitution of fluorine at a double bond by pentafluorophenoxy and heptafluoro-2-naphthoxy groups, respectively.Reduction of the resulting arylcyclohexadienones gave polyfluorinated phenols and naphthols with aryl and hydroxy groups in the 1,2-position.