Pd-Catalyzed Remote δ-C(sp2)–H Functionalization in Phenylalaninol: Expanding the Library of Phenylalaninols

Abstract

AbstractWe report the Pd(II)-catalyzed, picolinamide-directed δ-C(sp2)–H (ortho) functionalization of phenylalaninol scaffolds. Assembling of (ortho) δ-C–H arylated, alkylated, benzylated, alkenylated, brominated, and iodinated phenylalaninol scaffolds was accomplished. The δ-C(sp2)–H arylation reaction of phenylalaninol occurred under neat conditions. Hydrolysis of the picolinamide moiety and synthetic utility of the δ-C(sp2)–H arylated substrates were explored. We have also shown the preparation of some modified Matijin–Su (aurantiamide) derivatives using the bis δ-C–H (ortho) arylated phenylalaninol compounds obtained from the δ-C(sp2)–H arylation reaction (Matijin–Su is an anti-HBV agent possessing the phenylalaninol unit). Considering the importance of phenylalaninols, this work contributes to expanding the phenylalaninol library and demonstrates the substrate scope development in remote δ-C(sp2)–H functionalization reactions.