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Palladium-Catalyzed Oxidative Intermolecular Difunctionalization of Terminal Alkenes with Organostannanes and Molecular Oxygen

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  • This research was supported by the National Institutes of Health (NIGMS RO1 GM3540). M.S.S. thanks the Dreyfus Foundation (Teacher-Scholar Award) and Pfizer for their support. We are grateful to Johnson Matthey for the gift of various palladium salts. We thank Keith Gligorich for initial experiments.

Abstract

A cationic palladium complex catalyzes the title transformations, which are thought to proceed via a π-allyl or π-benzyl intermediate. The regioselectivity of the reaction (1,2- or 1,1-difunctionalization) depends on the type of terminal double bond (conjugated or nonconjugated) in the substrate (see scheme) and appears to be controlled by the relative rates of β-hydride elimination and transmetalation. DMA=dimethylacetamide, Tf=triflyl.

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