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Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C-H homocoupling of quinoline N-oxides.


ABSTRACT: 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.

SUBMITTER: Stephens DE 

PROVIDER: S-EPMC4714569 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C-H homocoupling of quinoline N-oxides.

Stephens David E DE   Lakey-Beitia Johant J   Chavez Gabriel G   Ilie Carla C   Arman Hadi D HD   Larionov Oleg V OV  

Chemical communications (Cambridge, England) 20150601 46


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. ...[more]

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