Synthesis of nitrogen heterocycles via Pd-catalyzed cross-coupling of o- alkenyl anilides with vinylic halides and triflates

Article abstract of DOI:10.1016/S0040-4020(98)00589-4

The palladium-catalyzed cross-coupling of o-allylic and o-vinylic anilides with vinylic halides and triflates produces substituted nitrogen heterocycles in good to high yields by a process involving vinylpalladium addition to the olefin, rearrangement to a π-allylpalladium intermediate and subsequent intramolecular nucleophilic displacement of palladium. Different reactivity and regioselectivity in the palladium migration have been observed with different substituted alkenyl anilides.