Synthesis of 3‑Chloroindoles via Palladium-Catalyzed Chlorocyclization of Unmasked 2‑Alkynylanilines

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-04 DOI:10.1002/adsc.202401296

Yongpeng Zheng, Jianxiao Li, Wanqing Wu, Chaorong Qi, Huanfeng Jiang

引用次数: 0

Abstract

Described herein is the discovery of a palladium-catalyzed chlorocylization strategy for the synthesis of 3‑chloroindoles tolerated with a wide range of functional groups in moderate to excellent yields. In this transformation, the solvent effect is so important that only THF presents the positive effect. Furthermore, the present method provides an essay access to the N-unprotected 3-chloroindoles. A mechanism study showed that 2-alkynlanilines were catalyzed by palladium to from corresponding indoles, followed by copper-mediated oxidation chlorination to deliver the 3-chloroindoles products.

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通过钯催化未掩蔽的 2-炔基苯胺的氯环化合成 3-氯吲哚

本文介绍了一种钯催化的氯酰化策略，该策略可用于合成具有多种官能团的 3-氯吲哚，收率从中等到极佳。在这一转化过程中，溶剂的作用非常重要，只有四氢呋喃具有积极的作用。此外，本方法还提供了获得 N-未保护的 3-氯吲哚的途径。机理研究表明，2-炔基苯胺在钯的催化下生成相应的吲哚，然后通过铜介导的氧化氯化反应得到 3-氯吲哚产物。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.