CO<sub>2</sub><sup>•–</sup> Enabled Synthesis of Phenanthridinones, Oxindoles, Isoindolinones, and Spirolactams

We report herein that photoinduced CO<sub>2</sub><sup>•-</sup> enabled reductive intramolecular radical cyclization of a variety of aryl iodide derivatives to the corresponding phenanthridinone, oxindole, isoindolinone, and spirolactam derivatives in good yields. Preliminary mechanistic studies suggested the generation of CO<sub>2</sub><sup>•-</sup> through homolysis of cesium formate in the presence of light, and the further involvement of CO<sub>2</sub><sup>•-</sup> and the aryl radical was directly proved by trapping with diphenyl styrene and TEMPO.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-28
DOI
https://doi.org/10.1021/acs.joc.4c02490
Citations
5
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
4.68

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article

CO2•– Enabled Synthesis of Phenanthridinones, Oxindoles, Isoindolinones, and Spirolactams

Veera Reddy Yatham, Vijay Kumar Simhadri, Rupam Sur
5 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
4.68
article

CO2•– Enabled Synthesis of Phenanthridinones, Oxindoles, Isoindolinones, and Spirolactams

Veera Reddy Yatham, Vijay Kumar Simhadri, Rupam Sur
article en
5 citations

Abstract

We report herein that photoinduced CO<sub>2</sub><sup>•-</sup> enabled reductive intramolecular radical cyclization of a variety of aryl iodide derivatives to the corresponding phenanthridinone, oxindole, isoindolinone, and spirolactam derivatives in good yields. Preliminary mechanistic studies suggested the generation of CO<sub>2</sub><sup>•-</sup> through homolysis of cesium formate in the presence of light, and the further involvement of CO<sub>2</sub><sup>•-</sup> and the aryl radical was directly proved by trapping with diphenyl styrene and TEMPO.

The Journal of Organic ChemistryVol. 90(10)
Indian Institute of Science Education and Research Thiruvananthapuram (IN)
Human Resource Development Group
Zero hunger
Openalex Percentile: Top 6%
Catalytic C–H Functionalization Methods
4.68
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