Nickel(0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines

J Org Chem. 2002 May 3;67(9):3029-36. doi: 10.1021/jo016352l.

Abstract

A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.