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 c...

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Main Authors: Stephens, David E, Lakey-Beitia, Johant, Chavez, Gabriel, Ilie, Carla, Arman, Hadi D, Larionov, Oleg V
Format: Article
Language:English
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc02227d