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

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).

SUBMITTER: Wolf C

PROVIDER: S-EPMC2531286 | biostudies-literature | 2006 Apr

REPOSITORIES: biostudies-literature

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

Wolf Christian C Liu Shuanglong S Mei Xuefeng X August Adam T AT Casimir Michael D MD

The Journal of organic chemistry 20060401 8

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 ev ...[more]

PMID: 16599627

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