Palladium(0)-catalyzed cyclopropane C–H bond functionalization: synthesis of quinoline and tetrahydroquinoline derivatives

Abstract

A series of quinoline and tetrahydroquinoline derivatives were prepared via a one-pot protocol involving intramolecular palladium(0)-catalyzed cyclopropane sp³ C–H bond functionalization and subsequent oxidation or reduction. The reaction conditions demonstrate good tolerance for a wide range of functional groups. Evidence suggests that the reaction proceeds through C–H bond cleavage and C–C bond formation to generate a dihydroquinoline intermediate via in situcyclopropane ring-opening.