Solvent-polarity-controlled stereoselective synthesis of cis-acyclic indoline via photocatalytic dearomatization of indole

作者：Yueteng Zhang, Menglong Li, Zhengpan Wei, Wen Ma, Lu Ma, Zhe Lei, Ziyuan Zhou, Zhiyuan Wang, Wei Wang, Kangdong Liu · 发表于：Green Synthesis and Catalysis · 年份：2025 · DOI：10.1016/j.gresc.2025.06.009 · 被引用次数：5 · 研究领域：Synthesis of Indole Derivatives、Oxidative Organic Chemistry Reactions、Radical Photochemical Reactions

Indolines, a privileged scaffold in natural products and bioactive molecules, hold immense potential in drug discovery and organic synthesis. Herein, we report a photocatalytic dearomatization strategy for the diastereoselective synthesis of unusual cis -2,3-disubstituted acyclic indolines from readily available indoles, aldehydes, and simple feedstocks. This method provides an efficient access to a diverse array of cis -acyclic indolines with high diastereoselectivity, which can be readily converted to their trans -isomers under alkaline conditions. Mechanistic studies reveal the critical role of solvent polarity in modulating isomerization rates, with low-polarity solvents retarding the cis -to- trans transformation. Notably, we uncover the unique photo-activated base properties of TBADT, offering new insights into photocatalytic processes. The biological evaluation demonstrates promising anti-cancer activity of products, underscoring the utility of this approach in medicinal chemistry. This work not only advances the synthesis of cis -indoline-based compounds but also opens new avenues for the development of bioactive molecules and functional materials.