Abstract
AbstractOxidized 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
Highlights
Quinoline synthesis is one of the most traditional methods to benchmark novel synthetic methodologies against both classical and more modern approaches
We report the synthesis of polysubstituted quinolines from o-vinyl anilines and aldehydes using a carbocatalyst, an oxidized active carbon, as a promoter
The catalytic activity of carbon materials are correlated to the distribution of O-containing functional groups (e. g., À COOH, C=O) on their surface, and, interestingly, their abundance can be fine-tuned by different oxidative treatments
Summary
Quinoline synthesis is one of the most traditional methods to benchmark novel synthetic methodologies against both classical and more modern approaches. Abstract: Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from ovinyl anilines and aldehydes.
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