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Alkoxyl Radicals Generated under Photoredox Catalysis: A Strategy for anti‐Markovnikov Alkoxylation Reactions
Author(s) -
Barthelemy AnneLaure,
Tuccio Béatrice,
Magnier Emmanuel,
Dagousset Guillaume
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201806522
Subject(s) - markovnikov's rule , photoredox catalysis , chemistry , radical , spin trapping , alkyl , photochemistry , cationic polymerization , catalysis , electron paramagnetic resonance , williamson ether synthesis , alkoxy group , ether , combinatorial chemistry , organic chemistry , regioselectivity , photocatalysis , physics , nuclear magnetic resonance
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.