Palladium-Catalyzed Direct Arylation of Allylamines with Simple Arenes

The Pd(OAc)(2)-catalyzed direct C-H bond olefination of unreactive arenes with allylamines in the presence of AgOAc was developed. A variety of allylamines including beta-substituted substrates underwent smooth coupling reactions with various arenes to give exclusively the terminal arylation products in high yields with excellent regioselectivities and stereoselectivities. The reaction is compatible with a range of functional groups in both coupling partners. The carbonyl group in the allylamine substrates is critical to catalysis, and the high regio- and stereocontrol observed is attributed to coordination between the carbonyl O and Pd atoms.