N-Heterocyclic Carbene/Organic Photoredox-Cocatalyzed Three-Component Tetralin Synthesis

We have developed the N-heterocyclic carbene/organic photoredox-cocatalyzed three-component tetralin synthesis using acyl fluorides and styrenes. The cooperative action of organic photoredox and NHC catalysis enabled the construction of the tetralin scaffold and the acylation of the benzylic position, yielding highly substituted tetralins with complete regioselectivity. Radical cation species, generated by single-electron oxidation of an alkene, were the key reaction intermediates. They subsequently reacted with another alkene and a ketyl radical intermediate to accomplish this transformation.

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Publication Details

Journal
Synlett
Published
2026-10-27
DOI
https://doi.org/10.1055/a-2991-6218
Primary Topic
Radical Photochemical Reactions
Type
article
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article

N-Heterocyclic Carbene/Organic Photoredox-Cocatalyzed Three-Component Tetralin Synthesis

Hirohisa Ohmiya, Sho Murakami, Yamato Goto, Kanata Togishi
2 links
Synlett
Radical Photochemical Reactions
article

N-Heterocyclic Carbene/Organic Photoredox-Cocatalyzed Three-Component Tetralin Synthesis

Hirohisa Ohmiya, Sho Murakami, Yamato Goto, Kanata Togishi
article en

Abstract

We have developed the N-heterocyclic carbene/organic photoredox-cocatalyzed three-component tetralin synthesis using acyl fluorides and styrenes. The cooperative action of organic photoredox and NHC catalysis enabled the construction of the tetralin scaffold and the acylation of the benzylic position, yielding highly substituted tetralins with complete regioselectivity. Radical cation species, generated by single-electron oxidation of an alkene, were the key reaction intermediates. They subsequently reacted with another alkene and a ketyl radical intermediate to accomplish this transformation.

Synlett
Kyoto University (JP)
Openalex Percentile: Top 26%
Radical Photochemical Reactions
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