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  • Title: Aryl-to-alkyl radical relay Heck reaction of amides with vinyl arenes.
    Author: Du YJ, Sheng XX, Li JH, Chen JM, Yang S, Chen M.
    Journal: Chem Sci; 2023 Mar 29; 14(13):3580-3586. PubMed ID: 37006700.
    Abstract:
    A palladium-catalyzed aryl-to-alkyl radical relay Heck reaction of amides at α-C(sp3)-H sites with vinyl arenes is described. This process displays a broad substrate scope with respect to both amide and alkene components and provides access to a diverse class of more complex molecules. The reaction is proposed to proceed via a hybrid palladium-radical mechanism. The core of the strategy is that the fast oxidative addition of aryl iodide and fast 1,5-HAT overcome the slow oxidative addition of alkyl halides, and the photoexcitation effect suppresses the undesired β-H elimination. It is anticipated that this approach would inspire the discovery of new palladium-catalyzed alkyl-Heck methods.
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