Electrochemical Dual Trifluoromethylation/Cyclization of 2-Aryl-N-acryloyl Indoles Enabling Assembly of Indole[2,1-a]isoquinolines

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI:10.1002/adsc.202401225

Haibo Mei, Yucheng Zhang, Jiang Liu, Jorge Escorihuela, Lorand Kiss, Jianlin Han

引用次数: 0

Abstract

An electrochemical cascade radical cyclization of 2-aryl-N-acryloyl indoles with sodium trifluoromethanesulfinate as a coupling partner has been explored, which afforded the unexpected bis-trifluoromethylated indole[2,1-a]isoquinolines as products. Experimental results and DFT calculations disclose that this reaction involves trifluoromethylation-triggered cyclization and the second trifluoromethylation as the key steps. This strategy does not need any transition-metal catalysts or oxidants with a readily available trifluoromethylating reagent enabling facile synthesis of bis-trifluoromethylated indole-fused tricycles.

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电化学双三氟甲基化/环化 2-芳基-N-丙烯酰基吲哚促成吲哚并[2,1-a]异喹啉的组装

研究人员探索了以三氟甲烷亚磺酸钠为偶联剂的 2-芳基-N-丙烯酰基吲哚的电化学级联自由基环化反应，其产物是意想不到的双三氟甲基化吲哚[2,1-a]异喹啉。实验结果和 DFT 计算表明，该反应的关键步骤包括三氟甲基化引发的环化和第二次三氟甲基化。这种策略不需要任何过渡金属催化剂或氧化剂，只需一种现成的三氟甲基化试剂，就能轻松合成双三氟甲基化吲哚融合三环化合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.