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).
Wolf
Christian
C
Department of Chemistry, Georgetown University, Washington, DC 20057, USA. cw27@georgetown.edu
Liu
Shuanglong
S
Mei
Xuefeng
X
August
Adam T
AT
Casimir
Michael D
MD
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
D000588:Amines; D003300:Copper; D019817:Benzoic Acid; D001966:Bromine