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1.2.3.2.2 Nickel Catalysis

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 1.2.3.1.2, 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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Me8 M8 M8 Meeee (%) Mee
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8-MeM8M8 (MM8)8M(MM8)8 88 [‌88‌]
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