Visible-Light-Mediated Cascade Arylcarboxylation/Cyclization of <i>N</i>-Aryl/Benzoyl Acrylamide with CO<sub>2</sub>

A visible-light-mediated radical cascade arylcarboxylation/cyclization of <i>N</i>-alkyl-<i>N</i>-methacryloylbenzamides and <i>N</i>-alkyl-<i>N</i>-arylmethacrylamides with carbon dioxide (CO<sub>2</sub>) was established. The reactions employed economical CO<sub>2</sub> as the carboxyl source, cesium carbonate as the base, triphenylsilane as the additive, and <i>fac</i>-Ir(ppy)<sub>3</sub> as the photocatalyst. Novel 1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-4-ylacetic acid derivatives and oxindole-3-acetic acid derivatives were obtained in moderate to good yields. This methodology shows a wide substrate scope, simple operation, excellent functional group compatibility, mild conditions, gram scale synthesis, and straightforward product derivatization. Detailed mechanistic insights reveal that CO<sub>2</sub><sup>•-</sup> generated <i>in situ</i> was invovled as key a key active intermediate under conditions free of external hydrogen atom transfer (HAT) and reducing agents.

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Publication Details

Journal
Organic Letters
Published
2025-07-26
DOI
https://doi.org/10.1021/acs.orglett.5c02172
Citations
8
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
Field-Weighted Citation Impact
5.64

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article

Visible-Light-Mediated Cascade Arylcarboxylation/Cyclization of N-Aryl/Benzoyl Acrylamide with CO2

Xinxin Ren, Azhar Iqbal, Weiwei Jin, Fei Xue et al.
8 citations
Organic Letters
Carbon dioxide utilization in catalysis
5.64
article

Visible-Light-Mediated Cascade Arylcarboxylation/Cyclization of N-Aryl/Benzoyl Acrylamide with CO2

Xinxin Ren, Azhar Iqbal, Weiwei Jin, Fei Xue, Chenjiang Liu, Ziren Chen, Bin Wang, Tao Zhang, Yonghong Zhang, Yu Xia, Shaofeng Wu
article en
8 citations

Abstract

A visible-light-mediated radical cascade arylcarboxylation/cyclization of <i>N</i>-alkyl-<i>N</i>-methacryloylbenzamides and <i>N</i>-alkyl-<i>N</i>-arylmethacrylamides with carbon dioxide (CO<sub>2</sub>) was established. The reactions employed economical CO<sub>2</sub> as the carboxyl source, cesium carbonate as the base, triphenylsilane as the additive, and <i>fac</i>-Ir(ppy)<sub>3</sub> as the photocatalyst. Novel 1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-4-ylacetic acid derivatives and oxindole-3-acetic acid derivatives were obtained in moderate to good yields. This methodology shows a wide substrate scope, simple operation, excellent functional group compatibility, mild conditions, gram scale synthesis, and straightforward product derivatization. Detailed mechanistic insights reveal that CO<sub>2</sub><sup>•-</sup> generated <i>in situ</i> was invovled as key a key active intermediate under conditions free of external hydrogen atom transfer (HAT) and reducing agents.

Organic LettersVol. 27(31)
Bacha Khan University (PK), Xinjiang Normal University (CN), China Jiliang University (CN), Xinjiang University (CN)
Natural Science Foundation of Xinjiang Province, National Natural Science Foundation of China, Shanghai Science International Cooperation Project
Openalex Percentile: Top 3%
Carbon dioxide utilization in catalysis
5.64
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