Buchwald-Hartwig cross-coupling reaction 

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The Buchwald-Hartwig cross-coupling reaction involves the reaction of an aryl halide (R-X) with an amine. The amine may have one or two R-groups on the nitrogen, and the R-groups may be aryl or alkyl groups. In the presence of a palladium catalyst and a strong base, often NaOtBu, these reagents form an aniline with a new C-N bond. The reaction is very general and widely used. The reaction makes similar products to the nucleophilic aromatic substitution, but the Buchwald-Hartwig coupling does not require electron-withdrawing groups to activate the aryl halide to attack by the amine.