He Zhengjun, Li Zhi, Lai Shuo, Li Hongji
Key Laboratory of Green and Precise Synthetic Chemistry, Ministry of Education, School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.
Org Lett. 2024 Aug 9;26(31):6652-6657. doi: 10.1021/acs.orglett.4c02307. Epub 2024 Jul 26.
We report a visible-light-promoted cyclization/sulfonylation cascade of -heterocycles with thianthrenium salts using DABSO as the SO surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration of bioactive relevant molecules. Mechanistic investigations reveal that the photoactive electron donor-acceptor (EDA) complexes between thianthrenium salts and DABCO are capable of the generation of aryl radicals, which induce the following SO insertion by attacking DABSO, thus triggering the key radical cyclization step.
我们报道了一种以DABSO作为SO替代物，可见光促进的-杂环与噻蒽鎓盐的环化/磺酰化串联反应。该方法具有出色的官能团耐受性、广泛的底物范围以及对生物活性相关分子的后期修饰能力。机理研究表明，噻蒽鎓盐与DABCO之间的光活性电子供体-受体（EDA）络合物能够生成芳基自由基，该自由基通过攻击DABSO引发后续的SO插入反应，从而触发关键的自由基环化步骤。
