Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines |
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Authors: | Wolf Christian Liu Shuanglong Mei Xuefeng August Adam T Casimir Michael D |
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Institution: | Department of Chemistry, Georgetown University, Washington, DC 20057, USA. cw27@georgetown.edu |
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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). |
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