Visible-Light-Driven C-3 Selenocyanation of Indoles with Elemental Selenium and TMSCN

作者：Yong‐Liang Ban, Xue Liu, Tao Huang, Xiaobing Liu, Ran Chen, Qinghong Li, Like Wang, Wei‐Wu Song, Qiang Liu · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c03266 · 被引用次数：7 · 研究领域：Sulfur-Based Synthesis Techniques、Radical Photochemical Reactions、Organoselenium and organotellurium chemistry

We develop a photocatalyst-free, visible-light-driven three-component reaction of indole, elemental selenium, and TMSCN in air at room temperature to synthesize indole 3-selenocyanoates. This protocol features eco-friendly, photocatalyst-free, elemental selenium, and TMSCN serves as the source of “SeCN”. Notably, the gram-scale reaction and product derivatizations demonstrated the practicality and effectiveness of this synergistic protocol. Preliminary mechanistic investigations indicate that light-absorbing species 2,3,4,6,7,8,9,10-octahydro-1 H -pyrimido[1,2- a ]azepin-5-ium selenocyanate is generated in situ from DBU, elemental selenium, and TMSCN.