文献类型：期刊文献

英文题名：Visible light-induced cascade annulation of sulfoxonium ylides with azides for the synthesis of 2-trifluoromethyl indoles

作者：Cui, Jia-Huan[1]; Chen, Qian-Yu[1]; Zhang, Jun[1]; He, Yan[2]; Li, Xingguang[1]; Liu, Pei-Nian[1,3]

机构：[1] Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai, 200237, China; [2] College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000, China; [3] State Key Laboratory of Natural Medicines, School of Pharmacy, China Pharmaceutical University, Nanjing, 210009, China

年份：2024

卷号：61

期号：3

起止页码：488

外文期刊名：Chemical Communications

收录：EI(收录号：20245017521701)

语种：英文

外文关键词：Addition reactions - Alkylation - Chlorination - Chromium compounds - Light metals - Reaction intermediates - Synthesis (chemical)

摘要：An efficient protocol was reported for the synthesis of 2-trifluoromethyl indoles through visible-light-promoted intermolecular cyclization of sulfoxonium ylides with azides, without the need for external photocatalysts, transition metals, or bases. The formation of 2-trifluoromethyl indoles involves an intriguing cascade process including azide rearrangement, intermolecular nucleophilic addition, and visible-light-promoted cyclization of a key intermediate. The protocol features high efficiency, mild conditions, excellent substrate compatibility and good regioselectivity. The practicality of this approach is demonstrated through scale-up reactions and further modifications of the synthesized indoles. ? 2025 The Royal Society of Chemistry.