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

Camille Banoun | Zendy; Flavien Bourdreux | Zendy; Emmanuel Magnier | Zendy; Guillaume Dagousset | Zendy

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

Author(s) -

Camille Banoun,

Flavien Bourdreux,

Emmanuel Magnier,

Guillaume Dagousset

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c03444

Subject(s) - chemistry , radical , alkoxy group , intermolecular force , photochemistry , enol , reactivity (psychology) , hydrogen atom , photoredox catalysis , catalysis , bond cleavage , medicinal chemistry , molecule , organic chemistry , alkyl , medicine , alternative medicine , pathology , photocatalysis

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.

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