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

Sophie Rousseaux (1) , Benoît Liégault (2) , Keith Fagnou (1)

1 University of Ottawa, Department of Chemistry
2 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier

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 situ cyclopropane ring-opening.

Domaines: Chimie organique; Catalyse

Sophie Rousseaux, Benoît Liégault, Keith Fagnou. Palladium(0)-catalyzed cyclopropane C-H bond functionalization: synthesis of quinoline and tetrahydroquinoline derivatives. Chemical Science, 2012, 3, pp.244-248. ⟨10.1039/C1SC00458A⟩. ⟨hal-00647081⟩