A new
strategy for the synthesis of fluorinated anilides in the
absence of metals and oxidants has been developed. This deoxyfluorination
of N-arylhydroxylamines with diethylaminosulfur trifluoride
(DAST) proceeded smoothly under mild conditions, and the ortho- or para-fluorinated aromatic amine products were
prepared in moderate to good yields. Structurally diverse fluorinated
anilides, including heterocyclic and pharmaceutically relevant molecules,
can be efficiently constructed by this protocol.