Visible‐Light‐Promoted Cascade Radical Cyclization for Difluorochroman‐4‐Ones Via Electron Donor‐Acceptor Complexes

Abstract The research of electron donor‐acceptor complex has developed fast in the field of photochemistry. Herein, the green and efficient metal‐free visible‐light‐promoted synthesis of difluorochroman‐4‐ones has been achieved with 2‐(allyloxy)arylaldehyde and bromodifluoroacetamide, which is driven by noncovalent interactions between 2‐(allyloxy)arylaldehyde/ N , N , N′ , N′ ‐tetramethylethylene diamine (TMEDA) and bromodifluoroacetamide/TMEDA. By precisely optimizing the electron donor and reaction solvent, a wide range of structurally diverse difluorochroman‐4‐ones, including aryl amide, aliphatic amide and ester groups, were obtained in up to 76 % yields. This strategy offers the benefits of simple operation, good yields, high atomic economy and broad applicability, providing an essential complement to traditional approaches for the preparation of chroman‐4‐one skeletons without any transition metals, photocatalysts or oxidants.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-08-19
DOI
https://doi.org/10.1002/ejoc.202400603
Citations
4
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.00

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article

Visible‐Light‐Promoted Cascade Radical Cyclization for Difluorochroman‐4‐Ones Via Electron Donor‐Acceptor Complexes

Qin‐Hua Song, Weifeng Wang
4 citations
European Journal of Organic Chemistry
Radical Photochemical Reactions
1.00
article

Visible‐Light‐Promoted Cascade Radical Cyclization for Difluorochroman‐4‐Ones Via Electron Donor‐Acceptor Complexes

Qin‐Hua Song, Weifeng Wang
article en
4 citations

Abstract

Abstract The research of electron donor‐acceptor complex has developed fast in the field of photochemistry. Herein, the green and efficient metal‐free visible‐light‐promoted synthesis of difluorochroman‐4‐ones has been achieved with 2‐(allyloxy)arylaldehyde and bromodifluoroacetamide, which is driven by noncovalent interactions between 2‐(allyloxy)arylaldehyde/ N , N , N′ , N′ ‐tetramethylethylene diamine (TMEDA) and bromodifluoroacetamide/TMEDA. By precisely optimizing the electron donor and reaction solvent, a wide range of structurally diverse difluorochroman‐4‐ones, including aryl amide, aliphatic amide and ester groups, were obtained in up to 76 % yields. This strategy offers the benefits of simple operation, good yields, high atomic economy and broad applicability, providing an essential complement to traditional approaches for the preparation of chroman‐4‐one skeletons without any transition metals, photocatalysts or oxidants.

European Journal of Organic ChemistryVol. 27(43)
University of Science and Technology of China (CN)
National Natural Science Foundation of China
Industry, innovation and infrastructure
Openalex Percentile: Top 27%
Radical Photochemical Reactions
1.00
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Visible‐Light‐Promoted Cascade Radical Cyclization for Difluorochroman‐4‐Ones Via Electron Donor‐Acceptor Complexes — Qin‐Hua Song, Weifeng Wang · European Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS