Nickel-Catalyzed Amination of Aryl Chlorides

Aryl chlorides are converted to aniline derivatives using catalytic amounts of Ni(COD)2 (COD = 1,5-cyclooctadiene) and DPPF (DPPF = 1,1‘-bis(diphenylphosphino)ferrocene) or 1,10-phenanthroline in the presence of sodium tert-butoxide. This procedure has a broad substrate scope: electron-rich or electron-poor aryl chlorides, as well as chloropyridine derivatives, can be combined with primary and secondary amines to give the desired aryl amine products in moderate to excellent yields. Additionally, a procedure which utilizes the air-stable precatalysts (DPPF)NiCl2 or (1,10-phenanthroline)NiCl2 is also described.