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Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis
Author(s) -
Wang MingMing,
Waser Jérôme
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202007864
Subject(s) - photoredox catalysis , hemiaminal , chemistry , fluorine , benzophenone , nucleophile , catalysis , ring (chemistry) , combinatorial chemistry , photochemistry , organic chemistry , photocatalysis
Abstract We report an oxidative ring‐opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the γ or δ position. Both inexpensive benzophenone with UVA light or organic and inorganic dyes with blue light could be used as photoredox catalysts to promote this process. Various fluorinated amines were then obtained by nucleophilic attack on the hemiaminals in one pot, giving access to a broad range of useful building blocks for medicinal chemistry.