A Photosensitizer-Free Radical Cascade for Synthesizing CF 3 -Containing Polycyclic Quinazolinones with Visible Light

Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of -cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any additional photosensitizer, metal, or extra additi...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-01, Vol.87 (2), p.1493-1501
Main Authors: Hu, Qiang, Yu, Wan-Lei, Luo, Yong-Chun, Hu, Xiu-Qin, Xu, Peng-Fei
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Light
Photosensitizing Agents
Quinazolinones
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Summary:Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of -cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any additional photosensitizer, metal, or extra additives. A series of trifluoromethyl quinazolinones were prepared efficiently with good yields and excellent functional group tolerance. Preliminary mechanistic experiments were conducted to indicate that the transformation proceeds via a possible mechanism involving photoexcited EDA complex and chain propagation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02889