Extending the substrate scope of palladium-catalyzed arylfluorination of allylic amine derivatives

Fluorinated molecules often show superior bioactivity or ADME (absorption, distribution, metabolism, and excretion) properties compared to their non-fluorinated analogues. In fact, 20-30 % of newly approved drugs and the majority of recently approved agrochemicals are organofluorine compounds. Unsur...

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Bibliographic Details
Published inJournal of fluorine chemistry Vol. 273; pp. 110239 - 110251
Main Authors Novak, Tamas T., Nguyen, Thi Cam Tu, Gomory, Agnes, Hornyanszky, Gabor, Remete, Attila Mario, Kiss, Lorand
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier 01.01.2024
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
Arylation
ACTIVATION
ACID
Alkenes
STRATEGY
Olefin difunctionalization
INTERMOLECULAR TRIFLUOROMETHYLARYLATION
INSIGHT
DISCOVERY
Arylfluorination
Palladium catalysis
CONSTRUCTION
FLUORINE
SCAFFOLDS
Fluorination
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Summary:Fluorinated molecules often show superior bioactivity or ADME (absorption, distribution, metabolism, and excretion) properties compared to their non-fluorinated analogues. In fact, 20-30 % of newly approved drugs and the majority of recently approved agrochemicals are organofluorine compounds. Unsurprisingly, there is great interest in the development of new and/or improved processes for fluorine incorporation. Pd-catalyzed arylfluorination of alkenes is a novel, emerging fluorination method, which simultaneously introduces a fluorine atom and an aryl group into an alkene framework. The aim of the current work was studying, improving, and extending a literature arylfluorination protocol, which originally utilized N-allylated sulfonamide substrates.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2023.110239