Photoinduced Remote C(sp 3 )–H Cyanation and Oxidation Enabled by a Vinyl Radical-Mediated 1,5-HAT Strategy

作者：Mengqi Luo, Shibo Zhu, Chengcheng Shi, Yunlong Du, Chao Yang, Lin Guo, Wujiong Xia · 发表于：Organic Letters · 年份：2022 · DOI：10.1021/acs.orglett.2c02523 · 被引用次数：23 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Oxidative Organic Chemistry Reactions

We report a vinyl radical-mediated 1,5-hydrogen atom transfer (1,5-HAT) strategy for the remote C(sp 3 )–H functionalization reaction, which includes cyanation, oxidation, and etherification under visible-light-induced photochemical conditions. This reaction is achieved using readily available alkyl N -hydroxyphthalimide esters as radical precursors, which can efficiently react with diverse alkynes to form key vinyl radical intermediates followed by a 1,5-HAT process. A series of structurally diverse γ-cyano, γ-carbonyl, and γ-oxygenated alkenes with excellent stereoselectivity can be efficiently constructed by this synthetic protocol.