C–H Diselenation and Monoselenation of Electron-Deficient Alkenes via Radical Coupling at Room Temperature

作者：Yao Chen, Mengxia Lv, Yuxin Zhang, Yao Wu, Linkun Ying, Jielin Tang, Xiangnan Gong, Jianmin Zhou, Zengqiang Song · 发表于：The Journal of Organic Chemistry · 年份：2022 · DOI：10.1021/acs.joc.2c01567 · 被引用次数：11 · 研究领域：Sulfur-Based Synthesis Techniques、Organoselenium and organotellurium chemistry、Catalytic C–H Functionalization Methods

A new, simple, and metal-free route for the diselenation of maleimides has been first developed employing (bis(trifluoroacetoxy)iodo)benzene (PIFA) at room temperature. The present method is compatible with different functional groups, and various diselenyl maleimides were obtained in moderate to excellent yields. Moreover, this protocol further highlights the unique practical application for the functionalization of biologically relevant molecules and amino acid derivatives. Preliminary mechanism studies suggest that radicals may be involved in this novel transformation. Additionally, this protocol is also applicable for the monoselenation of maleimides by switching the reaction conditions and selenation of other electron-deficient alkenes.