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Sterically Controlled, Palladium-Catalyzed Intermolecular Amination of Arenes

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journal contribution
posted on 12.06.2013, 00:00 by Ruja Shrestha, Paramita Mukherjee, Yichen Tan, Zachary C. Litman, John F. Hartwig
We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI­(OAc)2 as an oxidant in the presence of Pd­(OAc)2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.