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

Camille Banoun, Flavien Bourdreux, Emmanuel Magnier and Guillaume Dagousset*

*Université Paris-Saclay, UVSQ, CNRS, UMR 8180 Institut Lavoisier de Versailles, 78035 Versailles Cedex, France, Email: guillaume.dagoussetuvsq.fr

C. Banoun, F. Bourdreux, E. Magnier, G. Dagousset, Org. Lett., 2021, 23, 8921-8925.

DOI: 10.1021/acs.orglett.1c03444 (free Supporting Information)


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Abstract

Despite the high reactivity of alkoxyl (RO·) radicals and their propensity to easily undergo β-scission or Hydrogen Atom Transfer (HAT) reactions, an efficient photoredox-mediated intermolecular trapping of alkoxyl radicals by silyl enol ethers enables the introduction of both structurally simple and more complex alkoxy groups into a wide range of ketones and amides.


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proposed mechanism



Key Words

alkoxylation, α-hydroxylation


ID: J54-Y2021