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

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posted on 2022-10-11, 20:29 authored by Xiao-Feng Xia, Quan Huang, Tian-Yu Sun, Yuqin Jiang, Guoxia Ran
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.

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