Transition-Metal-Free Electrochemical Selenylative Cyclization of Alkynyl Phosphonates

作者：Bo Li, Yunhao Zhou, Yue Xu, Xiang Li, Zheyu Li, Linghui Gu, Wenbo Ma, Ruhuai Mei · 发表于：The Journal of Organic Chemistry · 年份：2023 · DOI：10.1021/acs.joc.3c01946 · 被引用次数：9 · 研究领域：Sulfur-Based Synthesis Techniques、Radical Photochemical Reactions、Catalytic C–H Functionalization Methods

Unprecedented regioselective electrochemical tandem selenation/cyclization of alkynyl phosphonates with diselenide is described here. These obtained selenoether products can be chemo-selectively converted into halogen-functionalized cyclic enol phosphonates under our electrochemical conditions. These protocols provide straightforward access to valuable cyclic enol phosphonate or phosphaisocoumarins under the electrochemical and transition-metal-free conditions. The robustness of these transformations was illustrated by their compatibility with various complex natural products and bioactive molecules. The selenoether and halogen functional groups allow the further diversification of the phosphorus heterocycles thus obtained.