Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone

The reaction between perfluorobenzophenone and aromatic amines proceeds with the substitution of one or more fluorine atoms. The regiochemistry of this substitution is controlled by solvent polarity, temperature, and nucleophilic character of the amine. o‐Anilinononafluorobenzophenone can be selectively transformed into acridines or acridones by using acid or base catalysis through electrocyclization or aromatic nucleophilic substitution. The reaction of decafluorobenzophenone with anilines produces the corresponding para‐anilino‐substituted derivatives, and the ortho/para ratio is strongly influenced by the donor number. The ortho isomers can be, in turn, selectively transformed into acridines and acridones under strongly acidic or basic conditions.