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使用CO作为切换试剂的2-芳基苯胺的底物控制的发散性还原环化反应

Substrate-Controlled Divergent Reductive Cyclization of 2-Arylanilines Using CO as a Switching Reagent.

作者信息

Yan Qiang, Nan Jiang, Cao Rui, Zhu Lanxin, Liu Shilei, Liang Chengyuan, Zhang Chen

机构信息

College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.

Xi'an Key Laboratory of Antiviral and Antimicrobial-Resistant Bacteria Therapeutics Research, Xi'an 710021, China.

出版信息

Org Lett. 2025 Jan 10;27(1):510-516. doi: 10.1021/acs.orglett.4c04538. Epub 2024 Dec 30.

Abstract

Capturing CO is highly valued in the field of organic synthesis, especially underdeveloped dual-CO conversion. In this study, we detail a novel reductive cyclization of 2-indolylanilines with dual CO as a difunctional reagent in the presence of PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective cyclization with 2-pyrrolylanilines is also realized by converting mono-CO. Mechanistic investigations shed light upon the fact that this substrate-controlled divergence mainly depends on the formation of -diacylative intermediates.

摘要

在有机合成领域,尤其是在欠发达的双CO转化中,捕获CO具有很高的价值。在本研究中,我们详细介绍了一种新型的2-吲哚基苯胺与双CO作为双官能试剂在聚甲基氢硅氧烷(PMHS)存在下的还原环化反应,生成甲基取代的喹喔啉。此外,通过转化单CO还实现了与2-吡咯基苯胺的另一种化学选择性环化反应。机理研究揭示了这样一个事实,即这种底物控制的分歧主要取决于二酰化中间体的形成。

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