Palladium(II)-Catalyzed Sequential Aminopalladation and Oxidative Coupling with Acetylenes/Enones: Synthesis of Newly Substituted Quinolines from 2-Aminophenyl Propargyl Alcohols

Palladium catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 3-alkynyl quinolines is realized via a cascade that involves aminopalladation, oxidative coupling with alkynes and dehydration. The method is shown to have a broad substrate scope with respect to propargyl alcohols as well as alkynes. Vinyl ketones as coupling partners in the same reaction afforded 3-alkenyl quinolines with equal ease.