Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Sulfoxonium Ylides for the Synthesis of α-Acetoxyl Ketones

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-07-11 DOI:10.1021/acs.orglett.4c01867
Qiwen Gao, Weiya Kong, Chen Chen, Jie Shi, Xingang Yao and Xiaodong Tang*, 
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Abstract

The most convenient and direct method of synthesizing an α-acyloxy ketone is the reaction of a diazo compound with a carboxylic acid via O–H insertion. However, due to the limitations in preparing and storing diazo compounds, the application of this method is restricted. In this study, Cu(OAc)2-mediated (OAc = acetate) decarboxylative coupling reactions of 3-indoleacetic acids with sulfoxonium ylides were developed for use in rapidly synthesizing α-acetoxyl ketones. In this reaction, Cu(OAc)2 was not only used as an oxidant, but also as acetate ion source. Notably, when 5-methoxy-2-methyl-3-indoleacetic acid reacted with different sulfoxonium ylides, the corresponding products exhibited fluorescence, and furthermore, several products displayed antiproliferative activities against various human cancer cell lines.

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铜介导的 3-吲哚乙酸与亚磺酰氧基锍的脱羧偶联,用于合成 α-乙酰氧基酮。
合成α-乙酰氧基酮最方便、最直接的方法是重氮化合物通过 O-H 插入与羧酸反应。然而,由于重氮化合物制备和储存的局限性,这种方法的应用受到了限制。本研究开发了 Cu(OAc)2 介导的(OAc = 乙酸酯)3-吲哚乙酸与磺酰氧鎓的脱羧偶联反应,用于快速合成 α-乙酰氧基酮。在该反应中,Cu(OAc)2 不仅用作氧化剂,还用作乙酸根离子源。值得注意的是,当 5-甲氧基-2-甲基-3-吲哚乙酸与不同的砜基酰化物反应时,相应的产物会发出荧光,此外,有几种产物对多种人类癌细胞株具有抗增殖活性。
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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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