Intermolecular C–O Bond Formation with Alkoxyl Radicals: Photoredox-Catalyzed α-Alkoxylation of Carbonyl Compounds
Camille Banoun, Flavien Bourdreux, Emmanuel Magnier, Guillaume Dagousset
Abstract
Due to the high reactivity of alkoxyl (RO·) radicals and their propensity to easily undergo β-scission or Hydrogen Atom Transfer (HAT) reactions, intermolecular alkoxylations involving RO· radicals are barely described. We report herein for the first time the efficient intermolecular trapping of alkoxyl radicals by silyl enol ethers. This photoredox-mediated protocol enables the introduction of both structurally simple and more complex alkoxy groups into a wide range of ketones and amides.
Topics & Concepts
ChemistryRadicalAlkoxy groupIntermolecular forcePhotochemistryEnolReactivity (psychology)Hydrogen atomPhotoredox catalysisCatalysisBond cleavageMedicinal chemistryMoleculeOrganic chemistryAlkylAlternative medicinePhotocatalysisMedicinePathologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques