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Activation of a C(sp3)[BOND]H Bond by a Transient σ-Alkylpalladium(II) Complex: Synthesis of Spirooxindoles Through a Palladium-Catalyzed Domino Carbopalladation/C(sp3)[BOND]C(sp3) Bond-Forming Process

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  • Financial support from EPFL (Switzerland), Swiss National Science Foundation (SNF), Swiss National Centres of Competence in Research (NCCR) and ICSN, CNRS (France) are gratefully acknowledged. T.P. thanks ICSN and EPFL for a doctoral fellowship. We thank Dr. Pascal Mieville for helpful discussion on NMR experiments.

Abstract

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Heck shortens the distance: A method for the palladium-catalyzed activation of a C(sp3)[BOND]H bond by a σ-alkyl PdII complex generated in situ from a remote arylhalide function has been developed. This approach allows a novel domino carbopalladation/C(sp3)[BOND]C(sp3) bond-forming process to provide rapid access to biologically relevant spirooxindoles.

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