Multicomponent Tf2O-Triggered Dearomative Triazinylmethylation of Isoquinolines Using Acetonitrile

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-02-13 DOI:10.1021/acs.joc.4c02834
Huazheng Wang, Yixin Chen, Shiqi Liu, Jiaxi Xu, Ning Chen
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Abstract

A Tf2O-triggered dearomative triazinylmethylation of isoquinolines and other azaarenes utilizing acetonitrile as the nucleophile has been developed through a formal five-component reaction. This method showcases a broad substrate scope and exceptional functional group compatibility, presenting a mild and expedient synthetic approach. Kinetic studies, including kinetic isotope effect (KIE) and Hammett analysis, indicate that the activation of isoquinolines by Tf2O constitutes the rate-limiting step.

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多组分tf20触发异喹啉类化合物乙腈脱芳三嗪基甲基化
以乙腈为亲核试剂,利用tf20触发异喹啉和其他氮杂环芳烃的脱芳三嗪甲基化反应。该方法具有广泛的底物范围和优异的官能团相容性,是一种温和而方便的合成方法。动力学研究,包括动力学同位素效应(KIE)和Hammett分析,表明Tf2O对异喹啉的活化是限速步骤。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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