Pyrone Isomerization Enabled Divergent Access to Multisubstituted Biaryl Phenol via Relay Claisen Rearrangement

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-01 DOI:10.1021/acs.orglett.5c01077

Jialin Wang, Mingluo He, Tongxiang Cao, Shifa Zhu

引用次数: 0

Abstract

Arene isomerization can simultaneously edit the arene backbone and its periphery, thereby bridging the independent chemistry of two distinct arenes. Herein, a facile pyrone isomerization approach for the divergent synthesis of five- and sixfold-substituted biaryl phenols is achieved by using a relay Claisen rearrangement as a crucial step. This catalyst-free isomerization reaction features high step, atom, and redox economy by transferring the innate oxidation state of pyrone into the biaryl phenols. Additionally, an intriguing self-activation phenomenon was observed, which enabled the selective dienone–phenol rearrangement of the aryl group.

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吡咯酮异构化通过继电克莱森重排实现了对多取代联芳基苯酚的发散获取

芳烃异构化可以同时编辑芳烃主链及其外围，从而将两种不同芳烃的独立化学连接起来。本文采用继电Claisen重排作为关键步骤，实现了一种简单的吡酮异构化方法，用于五和六重取代联芳基苯酚的发散合成。这种无催化剂异构化反应通过将吡酮的固有氧化态转化为联芳基酚，具有高阶、原子和氧化还原经济的特点。此外，观察到一个有趣的自激活现象，这使得芳基的选择性二烯酮-酚重排成为可能。

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

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.