Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated N-O/C-C bond cleavages and sequential radical-radical coupling  

作　　者：Ting Zou Yishu He Rui Liu Yihao Zhang Siping Wei Ji Lu Jun Wang Lin Wang Qiang Fu Dong Yi 

机构地区：[1]Department of Medicinal Chemistry,School of Pharmacy,Southwest Medical University,Luzhou 646000,China [2]Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province,Luzhou 646000,China [3]State Key Laboratory of Natural and Biomimetic Drugs,Peking University,Beijing 100191,China

出　　处：《Chinese Chemical Letters》2023年第5期222-226,共5页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.22101237,22171233,22001220);the Open Project Program of Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province(No.HYX21003);the Open Project Program of State Key Laboratory of Natural and Biomimetic Drugs(No.K202105);the Scientific Fund of Sichuan Province(Nos.2022NSFSC1219,21YYJC0697)。

摘　　要：A novel photoredox-neutral ring-opening pyridylation of non-prefunctionalized cyclic oximes has been accomplished through phosphoranyl radical-mediated N-O/C-C bond cleavages followed by radicalradical coupling.This mild acid-,base-,and oxidant-free protocol provides highly site-selective and efficient access to distally pyridylated alkylnitriles,which could be scale-up synthesized and readily converted into skeletally diverse compounds.Notably,the oxidized ground-state photocatalyst generated via the SET oxidation of the highly reducing excited-state photocatalyst by cyanopyridines might initiate the following phosphoranyl radical-mediated deoxygenative process.

关 键 词：Pyridylation Cyclic oxime Phosphoranyl radical Photoredox-neutral Radical-radical coupling 

分 类 号：O621.251[理学—有机化学]