Synthesis of Ester-Substituted Polycyclic N-Heteroaromatics via Photocatalyzed Alkoxycarbonylation/Tricyclization Reactions of Enediyne in Continuous Flow Conditions

Abstract

For the first time, a photoredox-catalyzed alkoxycarbonylation/tricyclization reaction was developed by employing readily accessible enediynes and alkyloxalyl chlorides as starting materials, enabling the synthesis of ester-substituted polycyclic N-heteroaromatics under mild conditions through a radical-mediated mechanism. This photocatalytic strategy is notable for its exceptional compatibility with diverse functional groups, scalability, and efficiency in the formation of rings and chemical bonds. Notably, continuous flow photocatalysis technology markedly improved these reactions compared to the equivalent batch reactions, efficiently decreasing the reaction times to merely 40 min.