Merging Photoredox Catalysis with Transition Metal Catalysis: Direct C4–H Sulfamidation of 1-Naphthylamine Derivatives,The Journal of Organic Chemistry

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Merging Photoredox Catalysis with Transition Metal Catalysis: Direct C4–H Sulfamidation of 1-Naphthylamine Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-08-13 , DOI: 10.1021/acs.joc.1c00635
Mengxue Pei ₁ , Conghui Zu ₁ , Zhen Liu ₂ , Fan Yang ₁ , Yangjie Wu ₁

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A mild and efficient protocol for the copper(I)-catalyzed C4–H sulfamidation of 1-naphthylamine derivatives with diphenylsulfonimide (NHSI) was explored at room temperature, affording the desire produces in moderate to good yields. The control experiments indicated that this visible-light-promoted reaction might proceed via a single-electron-transfer process. In addition, preliminary DFT studies for the intermediates in the catalytic cycle were also explored, indicating that the C4 site in the naphthyl ring is the most likely electrophilic reactive site and providing some exact basis for the plausible mechanism.

中文翻译：

将光氧化还原催化与过渡金属催化相结合：1-萘胺衍生物的直接 C4-H 磺酰胺化

在室温下探索了一种温和有效的方案，用于铜（I）催化的 1-萘胺衍生物与二苯磺酰亚胺（NHSI）的 C4-H 磺酰胺化，以中等至良好的产率提供所需的产物。对照实验表明，这种可见光促进的反应可能通过单电子转移过程进行。此外，还探索了催化循环中间体的初步 DFT 研究，表明萘环中的 C4 位点是最可能的亲电反应位点，并为可能的机制提供了一些确切的基础。

更新日期：2021-09-03

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