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.
Authors
- Xinxin Ren (ORCID: https://orcid.org/0000-0003-2797-1651)
- Azhar Iqbal (ORCID: https://orcid.org/0000-0002-5221-9384)
- Weiwei Jin (ORCID: https://orcid.org/0000-0002-5996-3229)
- Fei Xue (ORCID: https://orcid.org/0000-0002-9257-5076)
- Chenjiang Liu (ORCID: https://orcid.org/0000-0002-8241-0809)
- Ziren Chen (ORCID: https://orcid.org/0000-0002-3298-9584)
- Bin Wang (ORCID: https://orcid.org/0000-0002-8755-6401)
- Tao Zhang (ORCID: https://orcid.org/0009-0009-8039-5738)
- Yonghong Zhang (ORCID: https://orcid.org/0000-0002-7740-9408)
- Yu Xia (ORCID: https://orcid.org/0000-0002-0591-9169)
- Shaofeng Wu (ORCID: https://orcid.org/0009-0008-8396-1742)
Institutions
- Bacha Khan University (PK)
- Xinjiang Normal University (CN)
- China Jiliang University (CN)
- Xinjiang University (CN)
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
Funders
- Natural Science Foundation of Xinjiang Province
- National Natural Science Foundation of China
- Shanghai Science International Cooperation Project