College of Chemistry, Green Catalysis Center, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P. R. China.
School of Chemical Engineering, East China University of Science and Technology, Shanghai 200237, P.R. China.
J Org Chem. 2021 Sep 3;86(17):11324-11332. doi: 10.1021/acs.joc.1c00635. Epub 2021 Aug 13.
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.
探索了在室温下用二苯磺酰亚胺(NHSI)进行 1-萘胺衍生物的铜(I)催化 C4-H 磺酰胺化的温和高效的反应条件,以中等至良好的产率得到了所需产物。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,还对催化循环中的中间体进行了初步的 DFT 研究,表明萘环的 C4 位是最有可能的亲电反应位点,为合理的反应机制提供了一些确切的依据。