Catalytic C-N and C-H Bond Activation: ortho-Allylation of Benzoic Acids with Allyl Amines.

A facile insertion of ruthenium into aromatic C-H and allylic C-N bonds are the key steps in a [Ru( p-cymene)Cl2]2-catalyzed ortho-C-H allylation of benzoic acids. This protocol allows drawing on the large pool of allylic amines for state-of-the-art ortho-functionalizations of arenes, turning neutral amines into leaving groups. Concise syntheses of biologically active compounds provide further evidence of the synthetic potential of this methodology.