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Design of Organic Radical Cations as Potent Hydrogen‐Atom Transfer Catalysts for C−H Functionalization

Akira Matsumoto, Keiji Maruoka

2023Asian Journal of Organic Chemistry17 citationsDOIOpen Access PDF

Abstract

Abstract Hydrogen‐atom transfer (HAT) catalysis offers an atom‐ and step‐economical approach to the direct functionalization of aliphatic C−H bonds. While the structure of HAT catalysts largely affects the reactivity and selectivity in the step where the C−H bond is cleaved, the choice of viable catalysts for HAT from strong C−H bonds is limited. The recent development of organic HAT catalysts based on the flexibly modifiable molecular platform has enabled fine‐tuning of the steric and electronic properties of these catalysts, thus greatly expanding their structural diversity. This review focuses on the design of HAT catalysts with cationic moieties as common structural motifs and their application to the selective manipulation of the C−H bonds of challenging substrates, including unactivated hydrocarbons.

Topics & Concepts

ChemistryCatalysisSteric effectsSurface modificationReactivity (psychology)Cationic polymerizationHydrogen atomHydrogen bondSelectivityCombinatorial chemistryPhotochemistryStereochemistryOrganic chemistryMoleculePhysical chemistryGroup (periodic table)PathologyMedicineAlternative medicineRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCO2 Reduction Techniques and Catalysts
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