2-Pyridone-Enhanced Mn-Catalysis for the Synthesis of ortho-Deuterated Aromatic Nitriles.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-29 Epub Date: 2024-11-15 DOI:10.1021/acs.orglett.4c04061

Yanran Liu, Tao Qian, Jian-Fei Bai, Jinfeng Zheng, You Zhou, Zhi-Jiang Jiang, Jia Chen, Zhanghua Gao

引用次数: 0

Abstract

We herein present a method for the synthesis of ortho-deuterated aryl nitrile using Mn(CO)₅Br as catalyst with CH₃OD as deuteratium source, where the structure of aryl imidates is used for interconversion with a cyanide group. This method features a broad substrate range and excellent functional group tolerance, allowing late modification of various complex molecules with good yields and deuterium incorporation. Mechanistic studies suggest that 2-pyridone is crucial to the success of this chemistry, serving as an endogenous base that enhances the rate of hydrogen isotope exchange.

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2-Pyridone-Enhanced Mn-Catalysis for the Synhesis of ortho-Deuterated Aromatic Nitriles.

我们在此介绍一种以 Mn(CO)5Br 为催化剂、CH3OD 为氘源合成正氚代芳基腈的方法，其中芳基亚胺酸盐的结构用于与氰基的相互转化。该方法具有底物范围广、官能团耐受性好的特点，可对各种复杂分子进行后期改性，并具有良好的产率和掺氘效果。机理研究表明，2-吡啶酮对这种化学反应的成功至关重要，它是一种内源碱，能提高氢同位素交换的速率。

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.