2-炔基苯甲酸酯的三氟甲硫基化/硒化及内酯化反应：苄基三氟甲基亚砜/亚硒酰亚砜作为SCF/SeCF试剂的应用
Trifluoromethylthiolation/Selenolation and Lactonization of 2-Alkynylbenzoate: The Application of Benzyl Trifluoromethyl Sulfoxide/Selenium Sulfoxides as SCF/SeCF Reagents.
作者信息
Shi Haofeng, Wang Xingzong, Li Xiaoxian, Zhang Beibei, Li Xuemin, Zhang Jingran, Yang Jingyue, Du Yunfei
机构信息
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
Hebei Key Laboratory of State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, China.
出版信息
Org Lett. 2022 Mar 25;24(11):2214-2219. doi: 10.1021/acs.orglett.2c00563. Epub 2022 Mar 14.
The combined use of BnS(O)CF/BnSe(O)CF with TfO as SCF/SeCF reagents was implemented to realize an efficient synthesis of biologically interesting 4-(trifluoromethylthio/trifluoromethylseleno)isocoumarins from 2-alkynylbenzoates. The mechanistic pathway was postulated to involve formation of the electrophilic SCF/SeCF species via interrupted Pummerer reactions followed by a concerted trifluoromethylthiolation/selenolation and lactonization process.
将BnS(O)CF/BnSe(O)CF与TfO作为SCF/SeCF试剂联合使用，以实现从2-炔基苯甲酸酯高效合成具有生物学意义的4-(三氟甲硫基/三氟甲硒基)异香豆素。推测其反应机理是通过中断的Pummerer反应形成亲电SCF/SeCF物种，随后进行协同的三氟甲硫基化/硒化和内酯化过程。
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