title: Sterically controlled, palladium-catalyzed intermolecular amination of arenes.
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.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
authors.forename: Ruja
authors.initials: R
authors.lastname: Shrestha
authors.forename: Paramita
authors.initials: P
authors.lastname: Mukherjee
authors.forename: Yichen
authors.initials: Y
authors.lastname: Tan
authors.forename: Zachary C
authors.initials: ZC
authors.lastname: Litman
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000586:Amination; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010797:Phthalimides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001555:Benzene Derivatives; D009942:Organometallic Compounds; D010797:Phthalimides; D010165:Palladium