A Chelating Nucleophile Plays
a Starring Role: 1,8-Naphthyridine-Catalyzed
Polycomponent α,α-Difluorination of Acid Chlorides
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Abstract
A dually activated ketene enolate,
generated from an acid chloride,
the unusual chelating nucleophile (1,8-naphthyridine), and a Lewis
acid, reacts to afford a host of α,α-difluorinated products
in the presence of a benchtop-stable fluorinating agent (Selectfluor).
The use of this method to synthesize otherwise difficult to make products
is highlighted along with computational and spectroscopic support
for the proposed chelate