Aryl chlorides are converted to aniline derivatives using catalytic amounts of Ni(COD)2 (COD = 1,5-cyclooctadiene) and DPPF (DPPF = 1,1‚Äò-bis(diphenylphosphino)ferrocene) or 1,10-phenanthroline in the presence of sodium tert-butoxide. This procedure has a broad substrate scope:‚Äâ 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.
“Nickel-Catalyzed Amination of Aryl Chlorides”, J. Am .Chem .Soc., 1997, 119(26), 6054-6058.