Journal of Organic Chemistry 2006-04-14

Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines.

Christian Wolf, Shuanglong Liu, Xuefeng Mei, Adam T August, Michael D Casimir

Index: J. Org. Chem. 71(8) , 3270-3, (2006)

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Abstract

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).