PdII-Catalyzed Mild C-H ortho Arylation and Intramolecular Animation Oriented by a Phosphinamide Group

A novel protocol for the Pd-catalyzed ortho-arylation of aryl phosphinamide with boronic acid is reported. By using phosphinamide as a new directing group, the reaction proceeds efficiently under mild conditions at 40 degrees C. Mechanistic studies reveal that the reaction proceeds via a Pd-II to Pd-0 cycle. The phosphinamide group is also shown to be an effective orienting group for direct CH amination.