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. 2013 Jun 12;135(23):8480-3.
doi: 10.1021/ja4032677. Epub 2013 May 28.

Sterically controlled, palladium-catalyzed intermolecular amination of arenes

Ruja Shrestha  1 , Paramita Mukherjee, Yichen Tan, Zachary C Litman, John F Hartwig
Affiliations

Sterically controlled, palladium-catalyzed intermolecular amination of arenes

Ruja Shrestha et al. J Am Chem Soc. .

Abstract

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.

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