Photoinduced EDA Complexes Enabled C3 (Hetero)arylation of Indoles Using Amine as a Transient Occupying Group

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-08-28 DOI:10.1021/acs.orglett.5c03052

Anping Luo, Wenjie Liu, Jiaxin Yang, Jun Zhou, Sijia Zhang, Yimou Gong, Lin Yang, Yao Jian, Xia Zhou, Siping Wei* and Bowen Lei*,

引用次数: 0

Abstract

Herein, an EDA complex enabled selective C3 (hetero)arylation of indole was established, utilizing morpholine as the transient occupying group. This protocol is efficient, sustainable, and exhibits excellent substrate compatibility and functional group tolerance. Mechanistic studies revealed the binding of morpholine to the C2 position of the indole cation radical plays a key role in forming the transient radical at the C3 position. Furthermore, late-stage functionalization of biorelevant compounds and gram-scale synthesis demonstrate the utility of this protocol.

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光诱导EDA配合物以胺为暂态占位基使吲哚的C3（杂）芳基化

本文建立了一种EDA复合物，使吲哚选择性C3（杂）芳基化，利用啉作为短暂占位基团。该方案是有效的，可持续的，并表现出良好的底物相容性和官能团耐受性。机理研究表明，啉与吲哚阳离子自由基C2位置的结合在C3位置形成瞬时自由基中起着关键作用。此外，生物相关化合物的后期功能化和克级合成证明了该方案的实用性。

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.