Palladium-Catalyzed Z-Selective Oxidative Amination of ortho-Substituted Primary Anilines with Olefins under an Open Air Atmosphere

The Pd-catalyzed oxidative amination of olefins with primary anilines has been achieved using molecular dioxygen as the sole oxidant. The use of ortho-substituted primary anilines such as ortho-toluidine was the key to the successful development of this reaction, providing the corresponding N-alkenyl substituted anilines in high yields with unusually high levels of Z-selectivity.