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

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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.… Click to show full abstract

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.

Keywords: synthesis fluorinated; fluorohydroxylation ynamides; via direct; fluorinated imides; imides via

Journal Title: Organic letters
Year Published: 2019

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