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Direct C−H Radical Alkylation of 1,4‐Quinones
Author(s) -
Donzel Maxime,
Karabiyikli Deniz,
Cotos Leandro,
Elhabiri Mourad,
DavioudCharvet Elisabeth
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100452
Subject(s) - alkylation , chemistry , quinone , radical , photoredox catalysis , hydrogen atom abstraction , redox , combinatorial chemistry , halogen , photochemistry , catalysis , organic chemistry , photocatalysis , alkyl
1,4‐Quinones display unique redox and biological properties and have multiple applications in a wide array of fields, including health. Synthesis of diversely substituted quinone‐based compounds remains difficult and usually consists of multiple step sequences. Interest in direct C−H radical alkylation of 1,4‐quinones has thus continuously grown over this last decade. These reactions involve addition of carbon‐centered radicals generated from radical precursors through decarboxylative alkylation, hydrogen‐atom abstraction, or by carbon‐halogen bond reduction. Recent progresses in radical chemistry, including photoredox catalysis, have provided useful tools for quinone functionalization. This Minireview describes the recent progress with these methodologies, including the new promising three‐component cascade reactions involving quinones and alkenes, allowing for the preparation of complex substituted 1,4‐quinones in a single step.