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One-Pot Cross-Coupling/C–H Functionalization Reactions: Quinoline as a Substrate and Ligand through N–Pd Interaction

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posted on 23.01.2020, 19:05 by Rachel M. Shanahan, Aobha Hickey, Lorraine M. Bateman, Mark E. Light, Gerard P. McGlacken
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.