Photoredox Fe-Catalyzed Truce–Smiles Rearrangement of <i>N</i> -Arylsulfonyl Acrylamides with Aliphatic Carboxylic Acids

Herein, we report a photoredox Fe-catalyzed, redox-neutral Truce-Smiles rearrangement of <i>N</i>-arylsulfonyl acrylamides using readily available aliphatic carboxylic acids as radical precursors. This method accommodates a broad range of alkyl carboxylic acids, including difluoroacetic acid, enabling efficient access to functionalized amides that can be readily transformed into valuable CF<sub>2</sub>H-containing arylethylamines. The catalytic system is amenable to gram-scale synthesis, and mechanistic investigations support a radical-mediated mechanism involving intramolecular aryl migration.

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Publication Details

Journal
Organic Letters
Published
2025-10-27
DOI
https://doi.org/10.1021/acs.orglett.5c03932
Citations
3
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.81
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article

Photoredox Fe-Catalyzed Truce–Smiles Rearrangement of N -Arylsulfonyl Acrylamides with Aliphatic Carboxylic Acids

Depeng Duan, Niankai Fu, Song Lu, R. L. Huang
3 citations
Organic Letters
Radical Photochemical Reactions
2.81
article

Photoredox Fe-Catalyzed Truce–Smiles Rearrangement of N -Arylsulfonyl Acrylamides with Aliphatic Carboxylic Acids

Depeng Duan, Niankai Fu, Song Lu, R. L. Huang
article en
3 citations

Abstract

Herein, we report a photoredox Fe-catalyzed, redox-neutral Truce-Smiles rearrangement of <i>N</i>-arylsulfonyl acrylamides using readily available aliphatic carboxylic acids as radical precursors. This method accommodates a broad range of alkyl carboxylic acids, including difluoroacetic acid, enabling efficient access to functionalized amides that can be readily transformed into valuable CF<sub>2</sub>H-containing arylethylamines. The catalytic system is amenable to gram-scale synthesis, and mechanistic investigations support a radical-mediated mechanism involving intramolecular aryl migration.

Organic LettersVol. 27(44)
Zhejiang International Studies University (CN), Chinese Academy of Sciences (CN), Beijing National Laboratory for Molecular Sciences (CN), Careers Europe (GB), Institute of Chemistry (CN), Beihang University (CN)
Openalex Percentile: Top 9%
Radical Photochemical Reactions
2.81
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