Nickel-Catalyzed Benzylation of C-H Bonds in Aromatic Amides with Benzyltrimethylammonium Halides

Nickel-catalyzed benzylation reactions of C-H bonds in aromatic amides with benzyltrimethylammonium halides are developed by using a 5-chloro-8-aminoquinoline derivative as a bidentate directing group. Benzylation occurs selectively at the ortho-C-H bonds in aromatic amides, and no methylation was detected. The presence of a 5-chloro-8aminoquinoline moiety is essential for the success of this reaction, in which a variety of functional groups can be tolerated.