芳基卤化物与[MeN][SeCF]的光诱导三氟甲基硒化反应
Photoinduced Trifluoromethylselenolation of Aryl Halides with [MeN][SeCF].
作者信息
Li Fei, Han Xue, Xu Ziang, Zhang Cheng-Pan
机构信息
School of Chemistry, Chemical Engineering and Life Science, Hubei Key Laboratory of Nanomedicine for Neurodegenerative Diseases, Wuhan University of Technology, Wuhan 430070, China.
Department of Marine Engineering, School of Naval Architecture, Ocean and Energy Power Engineering, Wuhan University of Technology, Wuhan 430070, China.
出版信息
Org Lett. 2023 Nov 3;25(43):7884-7889. doi: 10.1021/acs.orglett.3c03116. Epub 2023 Oct 25.
A visible-light-induced metal-free trifluoromethylselenolation of aryl iodides and bromides with [MeN][SeCF] is described. The reaction was conducted at ambient temperature by successfully harnessing the light-sensitive SeCF reagent. Mechanistically, the EDA complexes between aryl halide and the SeCF anion or the base might be formed and excited by light, which subsequently undergo intracomplex SET processes to generate aryl and •SeCF radicals as key intermediates, allowing a convenient and green access to various aryl trifluoromethyl selenoethers.
本文描述了一种可见光诱导的无金属反应，即芳基碘化物和溴化物与[MeN][SeCF]发生三氟甲基硒化反应。该反应在室温下进行，成功利用了对光敏感的SeCF试剂。从机理上讲，芳基卤化物与SeCF阴离子或碱之间可能形成电子给体-受体（EDA）络合物，并被光激发，随后在络合物内部发生单电子转移（SET）过程，生成芳基和•SeCF自由基作为关键中间体，从而方便且绿色地合成各种芳基三氟甲基硒醚。
Zotero 插件