Carbamoylarylation of Alkenes with <i>N</i>-Aryl Oxamic Acids Involving 1,4-Aryl Migration Via C(aryl)–N Bond Cleavage

Abstract

We report carbamoylarylation of alkenes using N -aryl oxamic acid derivatives under visible-light irradiation. Reactions of alkenes with carbamoyl radicals generated using N -aryl oxamic acid derivatives to afford Giese-type products or 3,4-dihydroquinolin-2(1 H )-ones via ortho -radical addition to an aryl amide moiety have been previously reported. However, this study reveals that the introduction of a removable bulky group onto the nitrogen atom of N -aryl oxamic acids facilitates the radical addition of carbamoyl radicals to alkenes, resulting in 1,4-aryl migration via C(aryl)–N bond cleavage, thus affording arylpropanamides. Various alkenes, such as acrylic acid and styrene derivatives, are successfully applied to the synthesis of a variety of arylpropanamide derivatives, including 1,4-dicarbonyl amides, forming two C–C bonds.