Au(I)-Catalyzed Regioselective Hydrogen Isotope Labeling of Indoles

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-05 DOI:10.1021/acs.orglett.4c03597

Pierre Milcendeau, Pierre Colonna, Mohammed Ramdani, Sébastien Garcia-Argote, Nicolas Glinsky-Olivier, Grégory Pieters, Xavier Guinchard

引用次数: 0

Abstract

The gold(I)-catalyzed hydrogen isotope exchange reaction on indoles and related heterocycles is described under mild conditions and low catalyst loadings, using CD₃OD and D₂O as readily available deuterium sources. C3-unsubstituted indoles are labeled at the C3 position with exquisite regioselectivity, while C3-substituted indoles are labeled at the C2 position. The method is also applicable to the regioselective tritiation of indoles. Mechanistic studies revealed the involvement of aurated indoles as key intermediates.

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Au(I)-Catalyzed Regioselective Hydrogen Isotope Labeling of Indoles（金(I)催化的吲哚的区域选择性氢同位素标记

以 CD3OD 和 D2O 作为现成的氘源，描述了在温和条件和低催化剂负载下，金（I）催化的吲哚和相关杂环的氢同位素交换反应。C3 未取代的吲哚在 C3 位置被标记，具有极好的区域选择性，而 C3 取代的吲哚在 C2 位置被标记。该方法也适用于吲哚的区域选择性三烷基化。机理研究表明，醛化吲哚是关键的中间体。

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.