Palladium-catalyzed alkylation of ortho-C(sp ²)-H bonds of benzylamide substrates with alkyl halides

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.