Science of Synthesis

Guiry, P. J.; McCormack, P. J., Science of Synthesis, (2003) 5, 687.

In contrast to the α-C-arylation of phenols, the reaction of tris(acetoxy)arylplumbanes with arylamines in the presence of a copper catalyst affords products of N-monoarylation.[‌15‌,‌52‌] Moderate to good yields are obtained for a variety of anilines, although electron-poor anilines do not react. Sterically hindered substrates such as mesitylamine (‌34‌) give high yields (70–95%) of the corresponding diarylamines (‌Scheme 20‌). Heterocyclic amines react with tris(acetoxy)arylplumbanes to give modest yields of the N-aryl derivative, but aliphatic amines are N-arylated in poor yields (<10%).

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References