含苯并咪唑部分的活化烯烃与SFCl的底物控制五氟硫烷基化反应
Substrate-Controlled Pentafluorosulfanylation of Activated Alkenes Containing the Benzimidazole Moiety with SFCl.
作者信息
Tan Xinqiang, Li Yuezhen, Liu Shijie, Hao Ziyou, Guo Yingchang, Fan Ruiping, Yan Yunhui, Yuan Jianmei, Fang Lizhen, Zhou Ping-Xin, Tang Hao, Wang Yingling
机构信息
School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang, Henan 453003, P. R. China.
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035, P. R. China.
出版信息
J Org Chem. 2025 Apr 25;90(16):5499-5513. doi: 10.1021/acs.joc.5c00103. Epub 2025 Apr 14.
We report herein a method of substrate-controlled pentafluorosulfanylation of activated alkenes containing the benzimidazole moiety with SFCl, which provides a highly efficient way to access SF-containing benzo[4,5]imidazole[2,1-]isoquinolin-6(5)-ones, as well as SF-containing -benzoyl benzimidazoles. Besides the pentafluorosulfanyl group (-SF), the current method can be applied to the tetrafluorosulfanyl group (-SF-) incorporation. A radical mechanism involving single electron transfer (SET) or the atom transfer radical addition (ATRA) process is proposed.
我们在此报告一种利用SFCl对含苯并咪唑部分的活性烯烃进行底物控制的五氟硫烷基化方法，该方法为获得含SF的苯并[4,5]咪唑并[2,1 - ]异喹啉 - 6(5) - 酮以及含SF的 - 苯甲酰基苯并咪唑提供了一种高效途径。除了五氟硫烷基（-SF）外，该方法还可用于引入四氟硫烷基（-SF-）。我们提出了一种涉及单电子转移（SET）或原子转移自由基加成（ATRA）过程的自由基机理。
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