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Dearomatization through Photoredox Hydroarylation: Discovery of a Radical-Polar Crossover Strategy.

ABSTRACT: Indole dearomatization has been achieved via radical hydroarylation. Under mild photoredox conditions, a range of indole derivatives undergo hydroarylation to form 2-arylindoline products. Mechanistically, radical termination occurs primarily via stepwise reduction/protonation, with a small contribution from concerted hydrogen atom transfer. This mechanistic understanding prompted the extension of this reactivity to benzenoid dearomatization. This work formed the foundation of our program, which utilizes reductive radical-polar crossover to drive highly selective dearomatization pathways.

SUBMITTER: McDaniel KA

PROVIDER: S-EPMC8925927 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Dearomatization through Photoredox Hydroarylation: Discovery of a Radical-Polar Crossover Strategy.

McDaniel Kelly A KA Jui Nathan T NT

Organic letters 20210707 14

Indole dearomatization has been achieved via radical hydroarylation. Under mild photoredox conditions, a range of indole derivatives undergo hydroarylation to form 2-arylindoline products. Mechanistically, radical termination occurs primarily via stepwise reduction/protonation, with a small contribution from concerted hydrogen atom transfer. This mechanistic understanding prompted the extension of this reactivity to benzenoid dearomatization. This work formed the foundation of our program, which ...[more]

PMID: 34232663

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