Scope and Limitations of Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C-H Bonds

摘要

The scope of palladium-catalyzed, auxiliary-assisted direct arylation and alkylation of sp² and sp³ C-H bonds of amine and carboxylic acid derivatives has been investigated. The method employs a palladium acetate catalyst, substrate, aryl, alkyl, benzyl, or allyl halide, and inorganic base in t-amyl alcohol or water solvent at 100-140 °C. Aryl and alkyl iodides as well as benzyl and allyl bromides are competent reagents in this transformation. Picolinic acid auxiliary is used for amine γ-functionalization and 8-aminoquinoline auxiliary is used for carboxylic acid β-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.