Palladium(II)-Catalyzed Remote meta-C–H Functionalization of Aromatic Tertiary Amines

Pd­(II)-catalyzed remote C–H olefination of aromatic tertiary amines was achieved with high meta selectivity. With the assistance of an elaborated template, C–H functionalization of unreactive aryl tertiary amines, hindered by the p−π conjugation between the lone-pair electrons of the nitrogen atom and the phenyl ring, was realized with high meta regioselectivity via a quaternary ammonium salt assembly. The results demonstrate that apart from the distance and geometry of the template, the conformation of the arene substrate also plays a crucial role in the templated-assisted remote C–H functionalization.