Studies on the O/C-Arylation of Cyclic β-Diketones with Activated Aryl Fluorides

Article abstract of DOI:10.1002/prac.19933350111

The reaction of nitrosubstituted aryl fluorides 1 with cyclic β-diketones 2 proceeds at 20-80 deg C in the presence of bases, such as KOH, KF or NaOEt, leading to the aryl ethers 3a-m.Depending on the base the reaction of dimedone 2a or 1,3-cyclohexanedione 2b with 2,4-dinitrofluorobenzene 1a or 4-fluoro-3-nitrobenzonitrile 1b furnishes C- and/or O-arylated products.Upon heating of 3g, e and 3m at 40-100 deg C in DMF/K2CO3, the C-arylated ketones 4a-c are formed in good yields.Starting from 3a we obtained the chromenedione 5 under the same conditions.