Gao Yong, Hua Ruirui, Yin Hongquan, Chen Fu-Xue
School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.
Key Laboratory of Medical Molecule Science and Pharmaceutics Engineering, Ministry of Industry and Information Technology, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.
Org Biomol Chem. 2023 Mar 15;21(11):2417-2422. doi: 10.1039/d3ob00001j.
A tandem electrophilic thiocyanation and cyclization of arene-alkynes has been developed under mild conditions, affording thiocyanato-substituted phenanthrenes, dihydronaphthalenes, 2-chromenes and dihydroquinolines in moderate to excellent yields. This reaction provides an efficient protocol for the construction of C-SCN and C-C bonds in one step. In this transformation, -thiocyanato reagent serves as a convenient precursor to transfer SCN in the presence of trimethylchlorosilane, and the cyclization exhibited exclusive selectivity. Finally, a gram scale reaction and further derivatizations highlight the utility of this synthetic strategy.
在温和条件下开发了一种芳烃 - 炔烃的串联亲电硫氰化和环化反应，以中等到优异的产率得到硫氰酸根取代的菲、二氢萘、2-色烯和二氢喹啉。该反应为一步构建C-SCN和C-C键提供了一种有效的方法。在这种转化中，硫氰酸酯试剂在三甲基氯硅烷存在下作为转移SCN的便捷前体，并且环化表现出专一的选择性。最后，克级规模反应和进一步衍生化突出了这种合成策略的实用性。
