Tu Daoquan, Luo Jun, Jiang Chao
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, China.
Chem Commun (Camb). 2018 Mar 6;54(20):2514-2517. doi: 10.1039/c8cc00267c.
An efficient and cost-effective copper-mediated aerobic oxidative C-H iodination and nitration of indoles via double C-H functionalization is reported. The domino process proceeds smoothly under mild aerobic conditions to give 3-iodo-2-nitroindoles in one step with high regioselectivity and a broad substrate scope. The mechanism of the iodination step is proposed to proceed via a Cu(iii)-iodide species that undergoes electrophilic addition at the C3 position of the indole motif. The subsequent nitration step involves a sequence of C-H activation, nitro radical oxidative addition, and reductive elimination.
报道了一种通过双C-H官能化实现的高效且经济高效的铜介导的吲哚有氧氧化C-H碘化和硝化反应。该多米诺过程在温和的有氧条件下顺利进行，一步生成3-碘-2-硝基吲哚，具有高区域选择性和广泛的底物范围。碘化步骤的机理被认为是通过一种碘化铜（III）物种进行的，该物种在吲哚基序的C3位置发生亲电加成。随后的硝化步骤涉及一系列C-H活化、硝基自由基氧化加成和还原消除。
