A practical synthesis of α-fluorinated imides via the catalyst-free fluorohydroxylation of ynamides is developed. The reaction employs commercially available Selectfluor (F-TEDA-BF) and HO 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.
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