Palladium-Catalyzed Cascade Distal C–H Methylation and Cyclization for the Construction of Spirooxindole Skeletons

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-18 DOI:10.1021/acs.orglett.4c03315

Feng Wei, Yanghui Zhang

引用次数: 0

Abstract

Transition metal-catalyzed C–H methylation represents a straightforward approach for introducing methyl groups into organic molecules. Herein, we report a palladium-catalyzed alkene-relayed remote C–H methylation reaction that utilizes dimethyl carbonate as the methylation reagent. The aryl groups distal to a bromo group were dimethylated via C–H activation, leading to the formation of spirooxindoles as the final products through C(sp³)–H activation and C(sp³)–C(sp³) coupling. This cascade process involves the formation of four C–C bonds and the activation of three C–H bonds. The reaction not only provides a new approach to C–H methylation but also offers a novel method for constructing spirooxindole skeletons by merging skeleton construction and methylation into a single step.

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钯催化级联远端 C-H 甲基化和环化以构建螺吲哚骨架

过渡金属催化的 C-H 甲基化反应是将甲基引入有机分子的一种直接方法。在此，我们报告了一种利用碳酸二甲酯作为甲基化试剂的钯催化烯烃中继远程 C-H 甲基化反应。溴基远端芳基通过 C-H 活化被二甲基化，通过 C(sp3)-H 活化和 C(sp3)-C(sp3) 偶联形成螺吲哚作为最终产物。这一级联过程涉及四个 C-C 键的形成和三个 C-H 键的活化。该反应不仅为 C-H 甲基化提供了一种新方法，而且通过将骨架构建和甲基化合并为一个步骤，为螺吲哚骨架的构建提供了一种新方法。

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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.