Intermolecular C-O Bond Formation with Alkoxyl Radicals: Photoredox-Catalyzed α-Alkoxylation of Carbonyl Compounds

Camille Banoun (1) , Flavien Bourdreux (1) , Emmanuel Magnier (1) , Guillaume Dagousset (1)

1 ILV - Institut Lavoisier de Versailles

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.

Domaines: Chimie organique

Camille Banoun, Flavien Bourdreux, Emmanuel Magnier, Guillaume Dagousset. Intermolecular C-O Bond Formation with Alkoxyl Radicals: Photoredox-Catalyzed α-Alkoxylation of Carbonyl Compounds. Organic Letters, 2021, 23 (22), pp.8926-8930. ⟨10.1021/acs.orglett.1c03444⟩. ⟨hal-03487851⟩