Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2‐Vinyl Anilines
Mikko K. Mäkelä, Evgeny Bulatov, Kiia Malinen, Juulia Talvitie, Martin Nieger, Michele Melchionna, Anna Lenarda, Tao Hu, Tom Wirtanen, Juho Helaja
Abstract
Abstract 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. magnified image