Intercepting Hydrogen Evolution with Hydrogen-Atom Transfer: Electron-Initiated Hydrofunctionalization of Alkenes
Xiangyu Wu, Cara N. Gannett, Jinjian Liu, Rui Zeng, Luiz F. T. Novaes, Hongsen Wang, Héctor D. Abruña, Song Lin
Abstract
Hydrogen-atom transfer mediated by earth-abundant transition-metal hydrides (M-Hs) has emerged as a powerful tool in organic synthesis. Current methods to generate M-Hs most frequently rely on oxidatively initiated hydride transfer. Herein, we report a reductive approach to generate Co-H, which allows for canonical hydrogen evolution reactions to be intercepted by hydrogen-atom transfer to an alkene. Electroanalytical and spectroscopic studies provided mechanistic insights into the formation and reactivity of Co-H, which enabled the development of two new alkene hydrofunctionalization reactions.
Topics & Concepts
ChemistryHydrogen atomHydrogenElectron transferElectronPhotochemistryAtom (system on chip)Chemical physicsAtomic physicsOrganic chemistryNuclear physicsEmbedded systemAlkylComputer sciencePhysicsMetalloenzymes and iron-sulfur proteinsElectrocatalysts for Energy ConversionCO2 Reduction Techniques and Catalysts