You have the aryl bromide. You need the corresponding aniline. Buchwald-Hartwig isn’t working.

Been there. Done that. Got the t-shirt.

What to do? Check this out! A catalytic Ullman amination. No need for stochiometric amounts of copper. Ligand and solvent free. Table 3, entry 1, for instance.

JOC 2011, Article ASAP (Available here.)

The only caveat as I see it, from a quick glance, it that the reaction only proceeds in the presence of the “right amount” of air. To little or too much air, and the reaction halts. This probably means you want to stay within the Cu(I) <-> Cu(III) cycle, and not in Cu(0) <-> Cu(II) — or what do you think?

 

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