Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-16 DOI:10.1021/acs.orglett.4c03928
Yuta Niki, Koichi Mitsudo, Eisuke Sato, Seiji Suga
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Abstract

Catalysts for Claisen rearrangement have been intensively studied to overcome the need for high temperature. However, previous studies have encountered challenges, such as the need for heating, a long reaction time, and/or the need for equivalent amounts of catalyst. In this study, we introduce an effective electrogenerated boron-based Lewis acid catalyst for the aromatic Claisen rearrangement, which proceeds in a few minutes at ambient temperature. Generation of the electrogenerated Lewis acid catalyst is discussed based on NMR analysis and DFT calculations.

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为了克服对高温的需求,人们对用于克莱森重排的催化剂进行了深入研究。然而,以往的研究遇到了一些挑战,如需要加热、反应时间长和/或需要等量的催化剂。在本研究中,我们为芳香族克莱森重排引入了一种有效的电生硼基路易斯酸催化剂,该催化剂可在环境温度下几分钟内完成反应。我们根据核磁共振分析和 DFT 计算讨论了电生路易斯酸催化剂的生成。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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