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September 19, 2007Journal of the American Chemical Society608 citations

Elements of Regiocontrol in Palladium-Catalyzed Oxidative Arene Cross-Coupling

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DSDavid R. StuartEVElisia VillemureKFKeith Fagnou

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Abstract

By changing the stoichiometric oxidant and modifying the indole N -substituent in palladium-catalyzed oxidative arene cross-coupling reactions, both C2 and C3 oxidative indole arylation can be achieved in high yield. High regioselectivity can also be achieved with the benzene component, and the use of this methodology with pyrrole substrates is illustrated. A mechanistic hypothesis for the change in C2/C3 selectivity is advanced.

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Stuart et al. (2007) studied this question.

synapsesocial.com/papers/6a636cf5c1d5a33248096535https://doi.org/10.1021/ja0745862
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