芳基甲基醚甲氧基同位素交换的酸/碱催化官能团易位法

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-15 DOI:10.1021/acs.orglett.6c04029

Bu-Hong Zhang,Tong Wang,Zengyu Zhang,Chen-Yuan Li,Xiaoyu Yan

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引用次数: 0

摘要

摘要本文报道了一种用标记甲醇作为同位素源进行芳基甲基醚中甲氧基直接同位素交换的实用方法。碱催化体系（t-BuOK/18-冠-6）对缺电子底物有效，而酸催化体系（MeOTf）对富电子底物最有效。两种方案都能提供高产量的氘化产物，并且氘掺入率很高。通过标记药物分子并作为HPLC-MS /MS分析的内部标准，证明了其实用性。

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Acid/Base-Catalyzed Functional Group Metathesis Approach to Methoxy Group Isotopic Exchange of Aryl Methyl Ethers

Abstract We report a practical method for the direct isotopic exchange of methoxy groups in aryl methyl ethers using labeled methanol as an isotope source. A base-catalyzed system (t-BuOK/18-crown-6) is effective for electron-deficient substrates, whereas an acid-catalyzed system (MeOTf) is optimal for electron-rich substrates. Both protocols afforded deuterated products in high yields with excellent deuterium incorporation. The utility is demonstrated by labeling drug molecules and serving as an internal standard for HPLC–MS/MS analysis.

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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.