Electrolytic Partial Fluorination of Organic Compounds. 12. Selective Anodic Monofluorination of Fluoroalkyl and Alkyl Sulfides

Article abstract of DOI:10.1021/jo00099a023

Highly regioselective anodic monofluorination of various aryl and alkyl fluoroalkyl sulfides was successfully carried out, and fluorine was exclusively (aryl sulfides) or preferentially (alkyl sulfides) introduced at the position α to the fluoroalkyl group.Even simple alkyl phenyl sulfides devoid of an electron-withdrawing group could be anodically monofluorinated in satisfactory yields for the first time when etheral solvents were used as an electrolytic solution.A unique Pummerer-type mechanism via fluorosulfonium ions was proposed for this anodic fluorination by comparison with anodic α-methoxylation previously studied.