Gold-Catalyzed 1,2-Carboxyarylation of Alkenes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-24 DOI:10.1021/acs.orglett.5c00288

Tanmayee Nanda, Avishek Das, Prafulla Bera, Nitin T. Patil

引用次数: 0

Abstract

Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization of C–C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key to achieving this transformation is the use of a 1,3-diketone-appended alkene, which undergoes gold-catalyzed oxyarylation followed by retro-aldol reaction to afford the product. Detailed mechanistic investigations were conducted to support the proposed mechanism.

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在此，我们揭示了一种前所未有的金催化 1,2-羧基芳基化烯烃的方法，该方法是通过配体使金（I）/金（III）催化实现的。与其他对 C-C 多键进行芳基化官能团化的方法不同，利用弱亲核物（如羧酸阴离子）的尝试并不成功。实现这种转化的关键在于使用 1,3-二酮添加的烯烃，该烯烃在金催化下发生氧芳基化反应，然后进行反醛反应，最终得到产物。为支持所提出的机理，我们进行了详细的机理研究。

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.