Development of -F fluorinating agents and their fluorinations: Historical perspective.

This review deals with the historical development of all -F fluorinating agents developed so far. The unique properties of fluorine make fluorinated organic compounds attractive in many research areas and therefore fluorinating agents are important. -F agents have proven useful by virtue of their easy handling. This reagent class includes many types of -F compounds: perfluoro--fluoropiperidine, -fluoro-2-pyridone, -fluoro--alkylarenesulfonamides, -fluoropyridinium salts and derivatives, -fluoroquinuclidium salts, -fluoro-trifluoromethanesulfonimide, -fluoro-sultams, -fluoro-benzothiazole dioxides, -fluoro-lactams, -fluoro--benzenedisulfonimide, -fluoro-benzenesulfonimide, 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, -fluoropyridinium-2-sulfonate derivatives, 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane salts, -fluorodinitroimidazole, -fluoro-trichloro-1,3,5-triazinium salt, -F ethano-Tröger's base derivatives, -fluoro-methanesulfonimide, -fluoro--arylarenesulfonamides, bis-F salts such as ,-difluorobipyridinium salts and ,-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts, and their many derivatives and analogs, including chiral -F reagents such as optically active -fluoro-sultam derivatives, -fluoro-alkaloid derivatives, DABCO-based -F derivatives, and -F binaphthyldisulfonimides. The synthesis and reactions of these reagents are described chronologically and the review also discusses the relative fluorination power of each reagent and their mechanisms chronicling developments from a historical perspective.