Catalytic Desaturation and β-Fluorination of Aliphatic Amides Enabled by an Oxidative-Promoted Bond Destabilization

Abstract

Described herein is the development of a desaturation and β-fluorination reaction of cyclic amides, which is achieved by an oxidative-promoted selective hydrogen atom-transfer/isomerization/electrophilic fluorination process. Moreover, the combination of an N-hydroxy catalyst and Selectfluor allows α, β-dehydrogenation and γ-di-fluorination of N-aryl lactams to be established. Furthermore, the present selective catalysis also works well for the C–N bond cleavage of acyclic amides at the less-crowded site. The mechanism of this reaction has been carefully illustrated with experimental and computational studies.

Topics & Concepts