title: Palladium-catalyzed alkylation of ortho-C(sp2)-H bonds of benzylamide substrates with alkyl halides.
abstract: A highly efficient and generally applicable method has been developed to functionalize the ortho-C(sp(2))-H bonds of picolinamide (PA)-protected benzylamine substrates with a broad range of β-H-containing alkyl halides. Sodium triflate has been identified as a critical promoter for this reaction system. The PA group can be easily installed and removed under mild conditions. This method provides a new strategy to prepare highly functionalized benzylamines for the synthesis of complex molecules.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
authors.forename: Yingsheng
authors.initials: Y
authors.lastname: Zhao
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D010165:Palladium