title: Palladium-Catalyzed C-H Arylation of α,β-Unsaturated Imines: Catalyst-Controlled Synthesis of Enamine and Allylic Amine Derivatives.
abstract: A unique chemo- and regioselective α- and γ-arylation of palladium azapentadienyl intermediates is presented. Two distinct catalysts and sets of conditions successfully controlled the regioselectivity of the arylation. These methods provide the first umpolung C-H functionalization of azapentadienyl palladium intermediates and enable the divergent synthesis of allylic amine and enamine derivatives, which are of significant interest in the pharmaceutical industry.
authors: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
authors: Minyan
authors: M
authors: Li
authors: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
authors: María
authors: M
authors: González-Esguevillas
authors: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
authors: Simon
authors: S
authors: Berritt
authors: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.|Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P.R. China.
authors: Xiaodong
authors: X
authors: Yang
authors: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA.
authors: Ana
authors: A
authors: Bellomo
authors: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, USA. pwalsh@sas.upenn.edu.
authors: Patrick J
authors: PJ
authors: Walsh
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000588:Amines; D007097:Imines; D010165:Palladium
keywords: allylic amines; arylation; divergent synthesis; enamines; regioselectivity