通过乙烯基自由基介导的1,5-氢原子转移实现的光诱导远程C(sp)-H亚胺化反应
Photoinduced Remote C(sp)-H Imination Enabled by Vinyl Radical-Mediated 1,5-Hydrogen Atom Transfer.
作者信息
Li Shan-Shan, Jiang Yu-Shi, Luo Xue-Ling, Pan Cheng-Xue, Xia Peng-Ju
机构信息
School of Chemistry and Pharmaceutical Sciences, State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Guangxi 541004, People's Republic of China.
出版信息
Org Lett. 2023 Mar 10;25(9):1595-1599. doi: 10.1021/acs.orglett.3c00510. Epub 2023 Feb 24.
A vinyl radical-mediated 1,5-hydrogen atom transfer strategy for remote C(sp)-H imination under visible-light-induced photochemical metal-free conditions afforded diverse γ-imino alkenes with excellent stereoselectivity. Oxime ester-based bifunctional reagents provided not only nucleophilic alkyl radicals for radical addition reactions with electron-deficient alkynes but also long-lived steady-state imine radicals for trapping alkyl radicals following the intramolecular 1,5-hydrogen migration of unstable olefin radicals.
在可见光诱导的无金属光化学条件下，一种乙烯基自由基介导的用于远程C(sp)-H亚胺化的1,5-氢原子转移策略，以优异的立体选择性提供了多种γ-亚胺基烯烃。基于肟酯的双功能试剂不仅为与缺电子炔烃的自由基加成反应提供亲核烷基自由基，还为不稳定烯烃自由基的分子内1,5-氢迁移后捕获烷基自由基提供长寿命的稳态亚胺自由基。
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