4-Aryl-2-quinolones from 3,3-Diarylacrylamides through Intramolecular Copper-Catalyzed C–H Functionalization/C–N Bond Formation

Abstract

Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh₃, and KO-<i>t</i>-Bu in <i>o-</i>xylene at 100 °C. The reaction proceeds through a C–H functionalization/C–N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates where the aromatic ring <i>trans</i> to the amide group bears <i>o</i>-methyl, -chloro, or -bromo substituents