FACILE PREPARATION OF AROMATIC FLUORIDES BY DEAMINATIVE FLUORINATION OF AMINOARENES USING HYDROGEN-FLUORIDE COMBINED WITH BASES

One-pot deaminative fluorination of aminoarenes including heteroaromat ics, namely, diazotization of aminoarenes followed by in situ fluoro-d ediazoniation of the corresponding diazonium ions, was successfully ac complished to produce fluoroarenes in high yields by using hydrogen fl uoride combined with base solutions. The diazotization stage has been found to play the most important part in yielding fluoroarenes effecti vely. It was greatly influenced by the composition of the HF solution and enhanced by employing appropriate amounts of bases such as pyridin e under carefully controlled conditions. The fluoro-dediazoniation sta ge was effectively accelerated photochemically to afford fluoroarenes having polar substituents such as hydroxyl, nitro and so on in high yi elds.