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Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis. | LitMetric

Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis.

Angew Chem Int Ed Engl

Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.

Published: September 2020

AI Article Synopsis

Article 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.

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Source
http://dx.doi.org/10.1002/anie.202007864DOI Listing

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