title: Synthesis of anthranilic acid derivatives through iron-catalyzed ortho amination of aromatic carboxamides with N-chloroamines.
abstract: Arenes possessing an 8-quinolinylamide group as a directing group are ortho aminated with N-chloroamines and N-benzoyloxyamines in the presence of an iron/diphosphine catalyst and an organometallic base to produce anthranilic acid derivatives in high yield. The reaction proceeds via iron-catalyzed C-H activation, followed by the reaction of the resulting iron intermediate with N-chloroamine. The choice of the directing group and diphosphine ligand is crucial for obtaining the anthranilic acid derivative with high yield and product selectivity.
authors.affiliation: Department of Chemistry, School of Science, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Tatsuaki
authors.initials: T
authors.lastname: Matsubara
authors.forename: Sobi
authors.initials: S
authors.lastname: Asako
authors.forename: Laurean
authors.initials: L
authors.lastname: Ilies
authors.forename: Eiichi
authors.initials: E
authors.lastname: Nakamura
mesh_terms: D000577:Amides / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D002700:Chloramines / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D015394:Molecular Structure; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D002700:Chloramines; D005290:Ferric Compounds; D062367:ortho-Aminobenzoates; C031385:anthranilic acid