Regioselective Copper-Catalyzed Amination of Bromobenzoic Acids Using Aliphatic and Aromatic Amines

A chemo- and regioselective copper-catalyzed cross-coupling
procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection
and produces N-aryl and N-alkyl anthranilic acid derivatives
in up to 99% yield. N-(1-Pyrene)anthranilic acid has been
employed in metal ion-selective fluorosensing. Titration
experiments showed that this pyrene-derived amino acid
forms an equimolar complex with Hg(II) in water resulting
in selective fluorescence quenching even in the presence of
other metal ions such as Zn(II) and Cd(II).