Ruthenium-Catalyzed Carbonylation at Ortho C-H Bonds in Aromatic Amides Leading to Phthalimides: C-H Bond Activation Utilizing a Bidentate System

A new type of carbonylation of the ortho C-H bonds in aromatic amides 1, in which the pyridin-2-ylmethylamino moiety functions as a bidentate directing group, can be achieved. The presence of ethylene as a hydrogen acceptor and also of H2O, probably for the generation of an active catalytic species, is required. A wide variety of functional groups, including methoxy, amino, ester, ketone, cyano, chloro, and even bromo substituents, can be substituted for aromatic amides. The complex 9 was isolated by the stoichiometric reaction of 1b and Ru-3(CO)(12), in which I b binds to one Ru atom in the expected N,N fashion and the carbonyl oxygen binds to the other Ru atom as an O donor