Aerobic Oxidations via Organocatalysis: A Mechanistic Perspective
Haoran Li, Yongtao Wang, Jia Yao
Abstract
Abstract This review focuses on recent advances and mechanistic views of aerobic C(sp3)–H oxidations catalyzed by organocatalysts, where metal catalysis and photocatalysis are not included. 1 Introduction 2 Carbanion Route: TBD-Catalyzed C(sp3)–H Oxygenation 2.1 α-Hydroxylation of Ketones 2.2 Carbonylation of Benzyl C(sp3)–H 3 Radical Route: NHPI-Catalyzed C(sp3)–H Oxidation 3.1 N-Oxyl Radicals and Mechanisms 3.2 Oxygenation of Benzyl C(sp3)–H 3.3 Solvent Effects 4 Hydride-Transfer Route: TEMPO-Catalyzed Oxidations 4.1 Oxoammonium Cation and Mechanisms 4.2 Dehydrogenation of Alcohols 4.3 Oxygenation of Benzyl C(sp3)–H 5 Conclusions and Outlook
Topics & Concepts
ChemistryDehydrogenationHydroxylationCatalysisCarbanionCarbonylationOrganocatalysisRadicalMedicinal chemistryOrganic chemistryPhotochemistryCombinatorial chemistryEnantioselective synthesisEnzymeCarbon monoxideOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsVanadium and Halogenation Chemistry