Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C-H homocoupling of quinoline N-oxidesElectronic supplementary information (ESI) available: Experimental procedures and characterization data. CCDC 1037965. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5cc02227d

A novel site-selective palladium-catalyzed oxidative C8-H homocoupling reaction of quinoline N -oxides has been developed. The reaction affords substituted 8,8′-biquinolyl N,N ′-dioxides that can be readily converted to a variety of functionalized 8,8′-biquinolyls. Mechanistic studies point to the crucial role of the oxidant and a non-innocent behavior of acetic acid as a solvent. A novel site-selective palladium-catalyzed oxidative C8-H homocoupling reaction affords substituted 8,8′-biquinolyl N,N ′-dioxides that can be converted to functionalized 8,8′-biquinolyls.