N-Fluorobisimide: An Efficient Reagent for the α-Fluorination of Functionalized Carbonyl Compounds

Article abstract of DOI:10.1021/jo00016a022

The N-fluorobis<(trifluoromethyl)sulfonyl>imide (1) has been used in the electrophilic fluorination of the lithium enolate of esters, amides, and ketones.The corresponding α-fluorocarbonyl compounds have been obtained in good yields.The α-fluorination of β-diesters, β-diamides, β-keto esters, and β-diketones has been performed either on the neutral compounds or on the metal enolates.In this way some geminal azafluoro, chlorofluoro, fluorooxy compounds have been prepared in nearly quantitative yields.Also some α-keto esters and acids have been selectively monofluorinated in the β-position by simple treatment of the neutral compound with 1.