Photoredox-Catalyzed Aminolactonization of 2-Styrylbenzoic Acids with <i>N</i>-Aminopyridinium Salts to Access 4-Sulfonamino-3,4-dihydroisocoumarins

A photoredox-catalyzed aminolactonization of unsaturated carboxylic acids was achieved using <i>N</i>-aminopyridinium salts as the amino radical precursor. The transformation features mild conditions and a remarkably broad substrate scope, offering an efficient approach to construct a wide range of 4-sulfonamino 3,4-dihydroisocoumarins. Mechanistic studies indicate that the reaction proceeds via a distinctive <i>N</i>-aminopyridinium salt-promoted electrophilic amination of 2-styrylbenzoic acids.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-26
DOI
https://doi.org/10.1021/acs.joc.4c02473
Citations
8
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.00

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article

Photoredox-Catalyzed Aminolactonization of 2-Styrylbenzoic Acids with N-Aminopyridinium Salts to Access 4-Sulfonamino-3,4-dihydroisocoumarins

Wei‐Shiung Lian, Jinwei Yuan, Liangru Yang, Shouren Zhang et al.
8 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
2.00
article

Photoredox-Catalyzed Aminolactonization of 2-Styrylbenzoic Acids with N-Aminopyridinium Salts to Access 4-Sulfonamino-3,4-dihydroisocoumarins

Wei‐Shiung Lian, Jinwei Yuan, Liangru Yang, Shouren Zhang, Tong-Tong Bi, Qiang Liu, Wenyu Hu, Yan Meng
article en
8 citations

Abstract

A photoredox-catalyzed aminolactonization of unsaturated carboxylic acids was achieved using <i>N</i>-aminopyridinium salts as the amino radical precursor. The transformation features mild conditions and a remarkably broad substrate scope, offering an efficient approach to construct a wide range of 4-sulfonamino 3,4-dihydroisocoumarins. Mechanistic studies indicate that the reaction proceeds via a distinctive <i>N</i>-aminopyridinium salt-promoted electrophilic amination of 2-styrylbenzoic acids.

The Journal of Organic ChemistryVol. 90(1)
Henan University of Technology (CN), Huanghe Science and Technology College (CN)
Henan University of Technology, Natural Science Foundation of Henan Province
Clean water and sanitation
Openalex Percentile: Top 14%
Radical Photochemical Reactions
2.00
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Photoredox-Catalyzed Aminolactonization of 2-Styrylbenzoic Acids with <i>N</i>-Aminopyridinium Salts to Access 4-Sulfonamino-3,4-dihydroisocoumarins — Wei‐Shiung Lian, Jinwei Yuan, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS