Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines

Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold.

Automated summary

Oxidized active carbon catalyzes the formation of polysubstituted quinolines through a cascade manner involving condensation, electrocyclization, and dehydrogenation, allowing access to a wide range of quinolines. The metal-free catalytic procedure provides a heterogeneous protocol for the synthesis of various polysubstituted quinolines, with mechanistic studies indicating the importance of acid and quinoidic groups in oAC for the catalytic reaction.