Asymmetric Electrooxidation of Indoles: Mechanistic Insights from an Enantioselective Bromoradical Addition Pathway

作者：Changdi Zheng, Yanjun Wan, Yuhua Chen, Kaichun Wu, Yizhen Yin, Weihui Zhong, Fei Ling · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c03961 · 被引用次数：4 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Synthesis and bioactivity of alkaloids

Oxidative rearrangement of tetrahydro-β-carbolines (THβCs) represents a straightforward route to the synthesis of spirooxindoles. Herein, we disclose the first bromoradical (Br•)-initiated enantioselective electrooxidative rearrangement of THβCs, leading to highly enantioenriched spirooxindoles. Mechanistically, asymmetric Br• addition to THβCs initiates the reaction, distinguishing this process from established pathways induced by either halogen cations (X + ) or single-electron transfer (SET). Successful trapping of the key radical intermediate provides explicit evidence of this unprecedented Br•-mediated mechanism.