Synthesis of α-Fluorinated Imides via Direct Fluorohydroxylation of Ynamides.

A practical synthesis of α-fluorinated imides via the catalyst-free fluorohydroxylation of ynamides is developed. The reaction employs commercially available Selectfluor (F-TEDA-BF4) and H2O as the fluorine and hydroxyl sources, respectively. A broad range of aryl- or alkyl-substituted ynamides were well applicable to the reaction with good functional group tolerance under simple and mild reaction conditions. The synthetic utility of the α-fluoroimide products was demonstrated by several value-added transformations. Preliminary mechanistic studies were conducted.