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Radical Decarboxylative Fluorination of Aryloxyacetic Acids Using N ‐Fluorobenzenesulfonimide and a Photosensitizer
Author(s) -
Leung Joe C. T.,
Sammis Glenn M.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500038
Subject(s) - selectfluor , chemistry , photosensitizer , fluorine , organic chemistry , combinatorial chemistry , halogenation , catalysis
Fluorinated methoxy arenes are emerging as important motifs in both agrochemicals and pharmaceuticals. A novel technique for the synthesis of monofluoromethoxy arenes through the direct fluorodecarboxylation of carboxylic acids was developed that uses photosensitizers and N ‐fluorobenzenesulfonimide (NFSI). Utilization of the oxidatively mild fluorine transfer agent NFSI enabled the synthesis of fluoromethyl ethers that were previously inaccessible with decarboxylative fluorinations performed with Selectfluor. Mechanistic studies are consistent with the photosensitizer effecting oxidation of the aryloxyacetic acid.