N-Fluoro-1,4-Diazoniabicyclo[2.2.2]octane Dication Salts; Efficient Fluorinating Agents and Functionalization Mediators for Organic Compounds

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Fluorination of organic compounds using the most representative reagents from the group of N-fluoro-1,4-diazoniabicyclo[2.2.2]octane dication salts is reviewed. Data dealing with selective fluorofunctionalization of aromatics, alkenes, alkynes, saturated hydrocarbons, organometallics, and organic molecules bearing nitrogen, sulfur, phosphorus, silicon or carbonyl containing functional groups with SelectfluorTM F-TEDA-BF4 1 (1-chloromethyl- 4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra-fluoroborate)), Accufluor™ NFTh 2 (1-fluoro-4-hydroxy-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate)) or bis(NF)-TEDA-BF4 3 (1,4-difluoro-1,4-diazoniabicyclo[ 2.2.2]octane bis (tetrafluoroborate)) are systematically collected and comparatively evaluated. Fluorination of potentially bioactive organic molecules (steroids, pyrimidine bases, glycols …) with the above mentioned reagents is particularly emphasized. Functionalization of organic compounds mediated by Selectfluor™ F-TEDA-BF4 is briefly reviewed.