Cascade Synthesis of Phenanthrenes under Photoirradiation

We report a photoinduced phenanthrene synthesis from aryl iodides and styrenes through an arylation/cyclization cascade. Compared to prior methods, this approach obviates the need for hazardous reagents and provides access to unsymmetrical phenanthrenes with good functional group tolerance. Mechanis...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-01, Vol.88 (1), p.717-721
Main Authors: Li, Yongkang, Wise, Dan E., Mitchell, Joshua K., Parasram, Marvin
Format: Article
Language:English
Subjects:
Iodides
Molecular Structure
Phenanthrenes - chemistry
Styrenes - chemistry
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Summary:We report a photoinduced phenanthrene synthesis from aryl iodides and styrenes through an arylation/cyclization cascade. Compared to prior methods, this approach obviates the need for hazardous reagents and provides access to unsymmetrical phenanthrenes with good functional group tolerance. Mechanistic studies revealed that photoexcitation of aryl iodides leads to homolytic C–I bond cleavage. Arylation of styrenes with the formed aryl radical species furnishes stilbene derivatives, which undergo photoinduced cyclization promoted by iodine generated in situ to yield phenanthrene products.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02202