Rh(III)-Catalyzed Weakly Coordinating 2-Pyridone-Directed Oxidative Annulation Using Internal Alkynes: A Reversal in Selectivity
Satabdi Bera, Sanhita Sarkar, Juthi Pal, Rajarshi Samanta
Abstract
A rhodium(III)-catalyzed Satoh–Miura type oxidative annulation of N-aryl 2-pyridone derivatives is described using internal alkyne as a coupling partner. A weakly coordinating carbonyl group of the 2-pyridone ring is utilized for this transformation. The reaction proceeds with a broad scope and wide functional group tolerance. The solvent plays an important role in the developed method to furnish a different class of annulated product. A preliminary investigation was carried out to explore the photophysical properties of the obtained polyarylated N-naphthyl 2-pyridones.
Topics & Concepts
AnnulationChemistry2-PyridoneCatalysisRhodiumSelectivityFunctional groupOxidative coupling of methaneCombinatorial chemistryOxidative phosphorylationSolventArylRing (chemistry)Medicinal chemistryStereochemistryOrganic chemistryPolymerBiochemistryAlkylCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCatalytic Alkyne Reactions