Nickel-Catalyzed Reaction of Benzamides with Bicylic Alkenes: Cleavage of C-H and C-N Bonds

The nickel-catalyzed reaction of aromatic amides that contain an 8-aminoquinoline as a directing group with bicyclic alkenes, such as norbornene and 1,4-dihydro-1,4-epoxynaphthalene, results in the cleavage of both the C-H bond at the ortho-position of the benzene ring and the C(O)-N bond to give methanofluoren-9-one and 1,4-epoxyfluoren-9-one derivatives. Both Ni(OTf)(2) and Ni(cod)(2) show a high catalytic activity. The presence of AgOAc is essential for the reaction to proceed. In the meta-substituted aromatic amides, a less hindered C-H bond is exclusively functionalized.