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

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(1H)-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.