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

Abstract

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.