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Alkoxyl Radicals Generated under Photoredox Catalysis: A Strategy for anti-Markovnikov Alkoxylation Reactions

Anne-Laure Barthelemy 1 Beátrice Tuccio 2 Emmanuel Magnier 1 Guillaume Dagousset 1
1 ILV - Institut Lavoisier de Versailles
2 ICR - Institut de Chimie Radicalaire
Abstract : Reported herein is a novel photoredox-catalyzed approach for ether synthesis and it involves alkoxyl radicals generated from N-alkoxypyridinium salts. A wide range of alkenes are smoothly difunctionalized in an anti-Markovnikov fashion, affording various functionalized alkyl alkyl ethers. Notably, this mild process tolerates a number of functional groups and is efficiently carried out under both batch and flow conditions. Importantly, electron paramagnetic resonance (EPR) experiments by spin trapping were carried out to characterize the radical intermediates involved in this radical/cationic process.
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https://hal-amu.archives-ouvertes.fr/hal-02091883
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Submitted on : Saturday, April 6, 2019 - 5:16:57 PM
Last modification on : Tuesday, January 4, 2022 - 5:06:13 AM

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UNIV-AMU | CNRS | INC-CNRS | UVSQ | ILV | UNIV-PARIS-SACLAY | GS-CHIMIE

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Anne-Laure Barthelemy, Beátrice Tuccio, Emmanuel Magnier, Guillaume Dagousset. Alkoxyl Radicals Generated under Photoredox Catalysis: A Strategy for anti-Markovnikov Alkoxylation Reactions. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2018, 57 (42), pp.13790--13794. ⟨10.1002/anie.201806522⟩. ⟨hal-02091883⟩

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