Nickel or phenanthroline mediated intramolecular arylation of sp3 C-H bonds using aryl halides.

The development of the intramolecular arylation of sp(3) C-H bonds adjacent to nitrogen using aryl halides is described. Arylation was accomplished using either Ni(COD)2 or 1,10-phenanthroline in substoichiometric amounts, and the reaction conditions were applied to a variety of electronically differentiated benzamide substrates. Preliminary studies suggest a mechanism involving aryl and alkyl radical intermediates.