title: 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).
authors.affiliation: Department of Chemistry, Georgetown University, Washington, DC 20057, USA. cw27@georgetown.edu
authors.forename: Christian
authors.initials: C
authors.lastname: Wolf
authors.forename: Shuanglong
authors.initials: S
authors.lastname: Liu
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Mei
authors.forename: Adam T
authors.initials: AT
authors.lastname: August
authors.forename: Michael D
authors.initials: MD
authors.lastname: Casimir
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D000588:Amines; D003300:Copper; D019817:Benzoic Acid; D001966:Bromine