Synthesis of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process |
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Authors: | Pinto Artur Neuville Luc Retailleau Pascal Zhu Jieping |
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Affiliation: | Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France. |
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Abstract: | [reaction: see text] A highly efficient palladium-catalyzed synthesis of unsymmetrically substituted 3-(diarylmethylenyl)indolinones from readily accessible starting materials is developed. The domino reaction involves a sequence of intermolecular carbopalladation, C-H activation, and C-C bond formation. A plausible mechanistic pathway for the reaction is discussed on the basis of the kinetic isotope effect [K(H)/K(D) (intermolecular) = 1, K(H)/K(D) (intramolecular) = 2.7] as well as the electronic effect. |
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