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Updated: Jun 22, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Metal-Hydride C-C Cross-Coupling of Alkenes Through a Double Outer-Sphere Mechanism
Nathan Dao1,2, Xu-Cheng Gan1, Ryan A Shenvi1,2
1Department of Chemistry, Scripps Research, La Jolla, California 92037, United States.
None:
This Synopsis covers recent reports of metal-catalyzed alkene functionalizations that likely involve iterative outer-sphere reactions in which the substrate reacts directly with a metal ligand instead of with the metal center itself. Traditional metal hydride-catalyzed alkene functionalizations involve this latter pathway whereby the alkene forms part of the metal ligand sphere (i.e. an inner-sphere reaction). In contrast, alkenes do not ligate the metal in so-called outer-sphere reactions and instead react with a metal ligand. These transformations have proved crucial for the synthesis of high fraction sp3 (Fsp3) targets, especially in hindered fragment couplings of relevance to natural product space.
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