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酸催化的1,3-丁二炔基炔丙醇的三组分自发级联反应:一种合成酞嗪衍生物的方法

Acid-catalyzed, Three-component, Spontaneous Cascades of 1,3-Butadiynyl Propargylic Alcohols as a Route to Phthalan Derivatives.

作者信息

Shi Jingyang, Hoye Thomas R

机构信息

Department of Chemistry, University of Minnesota, 207 Pleasant St., SE, Minneapolis, Minnesota 55455.

出版信息

ACS Catal. 2025 Jul 18;15(14):12238-12246. doi: 10.1021/acscatal.5c03571. Epub 2025 Jul 6.

DOI:10.1021/acscatal.5c03571
PMID:40703645
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12281581/
Abstract

We have established an ambient temperature, one-pot, acid-catalyzed, three-component process involving in situ formation of a tetrayne or triyne that spontaneously cyclizes to a benzyne intermediate. This is rapidly captured to give a diverse range of polycyclic phthalan derivatives. Product structural diversity was enhanced by employing various combinations of alkyne substrates and benzyne trapping reagents. This cascade reaction is versatile and efficient and can be effected by a variety of Lewis and Brønsted acid catalysts. Success in an aqueous or even solvent-free environment was demonstrated.

摘要

我们已经建立了一种在环境温度下进行的、一锅法、酸催化的三组分反应过程,该过程涉及原位形成四炔或三炔,其可自发环化生成苯炔中间体。该中间体迅速被捕获,从而得到一系列多样的多环邻苯二甲酰衍生物。通过使用炔烃底物和苯炔捕获试剂的各种组合,增强了产物的结构多样性。这种串联反应具有通用性和高效性,并且可以由多种路易斯酸和布朗斯特酸催化剂实现。该反应在水性甚至无溶剂环境中也取得了成功。

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本文引用的文献

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Rapid (≤25 °C) cycloisomerization of anhydride-tethered triynes to benzynes - origin of a remarkable anhydride linker-induced rate enhancement.酸酐连接的三炔快速(≤25°C)环异构化为苯炔——酸酐连接基显著提高反应速率的原因
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