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.
