Ligand‐ and Base‐Free Cu‐Catalyzed C−N Coupling of Aminoquinolines with Boronic Acids

Abstract

A ligand-and base-free Cu-catalyzed protocol for the synthesis of N-arylquinolin-8-amine and N-arylquinolin-3-amine derivatives has been developed. A wide range of N-aryl heterocycles were synthesized in moderate to good yields under the mild condition of 10 mol% Cu(OAc) 2 in 3 mL methanol at room temperature in presence of air.

Recent advances in Chan–Lam coupling reaction

“…In the same year, Anilkumar et al developed a base-free and ligand-free Chan–Lam coupling protocol for the fabrication of N -arylquinolin-3-amine and N -arylquinolin-8-amine derivatives. 25 This C–N coupling was achieved by reacting 3- or 8-aminoquinolines with phenylboronic acids in the presence of 10 mol% Cu(OAc) 2 in MeOH at room temperature for 24 h under an air atmosphere, delivering the desired products in reasonable to good yields (Scheme 9). In the C–N coupling of 8-aminoquinolines and phenylboronic acids, unsubstituted boronic acids showed high reactivity.…”