Li Wan-Ting, Zhang Zhi-Xia, Huang Jing, Jiang Hui-Min, Luo Zhen-Wei, Li Jin-Heng, Ouyang Xuan-Hui
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, People's Republic of China.
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China.
Org Lett. 2024 Aug 9;26(31):6664-6669. doi: 10.1021/acs.orglett.4c02332. Epub 2024 Jul 30.
A photocatalytic method for the ring-closing 1,7-enyne metathesis using the α-amino radical as an alkene deconstruction auxiliary is present. Preliminary mechanistic studies suggest that intramolecular 1,5-hydrogen atom transfer is the key to the generation and β-scission of the α-amino radical, while the dearomatization of arenes and ring opening of cyclopropanes are the key to construct spirocyclic quinolin-2-ones. This approach highlights the potential of ring-closing 1,7-enyne metathesis, providing a green, efficient, and step-economical way for the synthesis of spirocyclic quinolin-2-ones.
本文报道了一种光催化的闭环1,7-烯炔复分解反应方法，该方法使用α-氨基自由基作为烯烃解构助剂。初步机理研究表明，分子内1,5-氢原子转移是α-氨基自由基生成和β-断裂的关键，而芳烃的去芳构化和环丙烷的开环是构建螺环喹啉-2-酮的关键。该方法突出了闭环1,7-烯炔复分解反应的潜力，为螺环喹啉-2-酮的合成提供了一种绿色、高效且步骤经济的方法。
