Rapid Access to Fluorinated Anilides via DAST-Mediated Deoxyfluorination of Arylhydroxylamines

Abstract

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.