Synthesis of Anthranilic Acid Derivatives through Iron-Catalyzed Ortho Amination of Aromatic Carboxamides with <i>N</i>‑Chloroamines

Abstract

Arenes possessing an 8-quinolinylamide group as a directing group are ortho aminated with <i>N</i>-chloroamines and <i>N</i>-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 <i>N</i>-chloroamine. The choice of the directing group and diphosphine ligand is crucial for obtaining the anthranilic acid derivative with high yield and product selectivity