Transition Metal‐Free, Base‐Induced Arylation of Amino Acids: Synthesis of N‐(para‐Substituted phenyl)amino‐2‐carboxylic acids

Abstract

AbstractA metal‐free aryl amination reaction of aryl halides and amino acids; with the amino acid serving as the nucleophilic aminating agent, is reported. The reaction was achieved by the condensation of various aryl halides 1 with cyclic and acyclic amino acids 2, in the presence of a cheap and readily available base, potassium carbonate, in refluxing ethanol/water solution (1 : 1) for 3 h, under simple operating conditions. The products, N‐(p‐substituted phenyl)‐amino‐2‐carboxylic acids 3–12, were obtained in isolated yields of 25–90% and characterized by IR, 1H‐ and 13C‐NMR spectroscopy and high‐resolution mass spectrometry. These arylated amino acids are vital synthons and precursors to many compounds of physiological importance.