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DOI: 10.1055/sos-SD-223-00066

Martin, A. R.Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis, (20161174.

In addition to the procedures discussed in Section, which are also relevant for the coupling of (het)aryl bromides and iodides, a well-defined nickel-based catalyst 37 is used for the arylation of amines with aryl bromides to give arylamines 38.[‌49‌] The employed bromide reagents can be electron-rich or electron-poor; hindered bromides were not surveyed. The amine partner is preferably an aniline derivative; morpholine reacts poorly. Moreover, the aniline partner cannot be too deactivated; 4-(trifluoromethyl)aniline does not undergo the reaction. Significant steric hindrance is tolerated on the aniline, mesitylamine is a very efficient reagent, although greater bulk is detrimental to the yield of the reaction (Scheme 17).

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