NICKEL-CATALYZED AMINATION OF ARYL CHLORIDES

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