Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-Catalyzed Cyclization/Olefination

A variety of 4-(1-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49−51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.