Efficient copper-catalyzed amination of aryl halides with amines and N-H heterocycles using rac-BINOL as ligand

A highly efficient copper-catalyzed system using commercially available racemic 1,1'-binaphthyl-2,2'-diol (rac-BINOL) as the ligand was developed for amination of aryl halides and heteroaryl halides with alkyl amines and N-H heterocycles. Good to high yields were obtained for aryl bromides and heteroaryl chlorides. The commercially available rac-BINOL ligand with excellent stability and high efficiency for aryl bromides and heteroaryl chlorides ultimately make this protocol of potentially practical utility. (c) 2006 Elsevier B.V. All rights reserved.