A Photosensitizer–Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light

Qiang Hu, Wan-Lei Yu, Yong-Chun Luo, Xiu-Qin Hu*, and Peng-Fei Xu*

https://doi.org/10.1021/acs.joc.1c02889

Abstract

Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of N-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.