Mechanism of Benzoquinone-Promoted Palladium-Catalyzed Oxidative Cross-Coupling Reactions
Journal of the American Chemical SocietyPublished 1 July 2009
Kami L. Hull, Melanie S. Sanford
Citations251
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Abstract
This communication describes mechanistic studies of the Pd-catalyzed oxidative cross-coupling of benzo[h]quinoline with simple arenes. Through a series of experiments, including determination of the order of the reaction in various reagents, H/D exchange studies, kinetic isotope effect investigations, and the evaluation of electronic effects, we propose a detailed mechanism for these reactions. Importantly, this mechanism explains the key role of benzoquinone in these transformations; in addition, it provides insights that allow the rational tuning of reaction conditions to control the chemoselectivity of Ar-Ar' coupling.
Keywords
Chemistry
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