Selective and efficient direct fluorination of polycyclic aromatic hydrocarbons using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Article abstract of DOI:10.1246/cl.1996.1077

A new N-F fluorinating reagent 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor NFTh) was effectively used for selective fluorination of polycyclic aromatics. Naphthalene was site-selectively fluorinated to 1-fluoronaphthalene, phenanthrene to 9-fluorophenanthrene, and pyrene to 1-fluoropyrene. In a series of substituted naphthalenes the regioselectivity and effectiveness of fluorination depended on the position and the nature of the substituents.