Liu Zhaosheng, Zhong Shuai, Ji Xiaochen, Deng Guo-Jun, Huang Huawen
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
Org Lett. 2022 Jan 14;24(1):349-353. doi: 10.1021/acs.orglett.1c04015. Epub 2021 Dec 14.
Metal- and additive-free photoredox cyclization of -arylacrylamides is herein reported that provides a concise access to the formation of dihydroquinolinones. In this protocol, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. This reaction system features exclusive 6- cyclization selectivity with a generally good yield of a range of functionalized dihydroquinolinones and dihydrobenzoquinolinones. Mechanistical studies reveal the feasibility of both 1,3-H shift and intersystem crossing of the diradical intermediate.
本文报道了无金属和添加剂的芳基丙烯酰胺光氧化还原环化反应，该反应为二氢喹啉酮的形成提供了一种简洁的方法。在该方案中，可持续可见光用作能源，有机发光分子4CzIPN用作高效光催化剂。该反应体系具有独特的6-环化选择性，一系列功能化二氢喹啉酮和二氢苯并喹啉酮的产率通常良好。机理研究揭示了双自由基中间体1,3-H迁移和系间窜越的可行性。
