Journal of Organic Chemistry p. 4925 - 4929 (1991)
Update date:2022-07-29
Topics:
Resnati, Giuseppe
DesMarteau, Darryl D.
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.
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