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

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...

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Bibliographic Details
Published in:ACS catalysis 2022-10, Vol.12 (20), p.12964-12972
Main Authors: Xia, Xiao-Feng, Huang, Quan, Sun, Tian-Yu, Jiang, Yuqin, Ran, Guoxia
Format: Article
Language:English
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c04014