One-Pot Cross-Coupling/C–H Functionalization Reactions: Quinoline as a Substrate and Ligand through N–Pd Interaction
Rachel Shanahan, Aobha Hickey, Lorraine M. Bateman, Mark E. Light, Gerard P. McGlacken
Abstract
Herein, we report a one-pot process that marries mechanistically distinct, traditional cross-coupling reactions with C–H functionalization using the same precatalyst. The reactions proceed in yields of up to 95%, in air, and require no extraneous ligand. The reactions are thought to be facilitated by harnessing the substrate quinoline as an N-ligand, and evidence of the palladium–quinoline interaction is provided by 1H-15N HMBC NMR spectroscopy and X-ray crystallographic structures. Application of the methodology is demonstrated by the quick formation of fluorescent, π-extended frameworks.
Topics & Concepts
ChemistryQuinolineLigand (biochemistry)Surface modificationPalladiumSubstrate (aquarium)Coupling reactionCombinatorial chemistryStereochemistryPhotochemistryCatalysisOrganic chemistryPhysical chemistryOceanographyGeologyReceptorBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions