Pd(II)-Catalyzed, Picolinamide-Aided γ-(sp2)-C-H Functionalization of Racemic and Enantiopure α-Methylbenzylamine and Phenylglycinol Scaffolds

In this paper, we report the Pd(II)-catalyzed, picolinamide DG-aided sp(2) gamma-C-H functionalization and expansion of the library of enantiopure alpha-methylbenzylamine and phenylglycinol scaffolds. We have shown the synthesis of a wide range of racemic and enantiopure ortho-C-H arylated, alkylated, brominated, and iodinated alpha-methylbenzylamine and phenylglycinol scaffolds. Various racemic and R and S (chiral) sp(2) gamma-C-H functionalized alpha-methylbenzylamine and phenylglycinol scaffolds were synthesized with good enantiopurities. Racemic and enantiopure alpha-methylbenzylamine and phenylglycinol derivatives are important building blocks in organic synthesis and medicinal chemistry. Accordingly, this work contributes to the expansion of the libraries of alpha-methylbenzylamine and phenylglycinol motifs and substrate scope development through the Pd(II)-catalyzed bidentate directing group picolinamide-aided site-selective C-H activation and functionalization method.