Nickel-Catalyzed Directed Benzylation of Ortho C-H Bonds in Aromatic Amides through C-H/C-N Cleavage

The cleavage of both sp(2) C-H and C-N bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety with benzyl ammonium salts is reported. A wide variety of functional groups are tolerated in the reaction. Preliminary mechanistic investigations indicate that the reaction probably proceeds through a Ni-I/Ni-III catalytic pathway. This Ni-catalyzed procedure provides an alternative approach to construct diarylmethane derivatives.