Deconstructive Dicarbofunctionalization of Cyclic Amines Enabled by C-H and C-N Bond Activation

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-03-21 DOI:10.1039/d5qo00270b

Qiming Zhu, Kaifang Wang, Yuyuan Fan, Tianze Zhang, Xianchen Song, Shuang Luo, Qiang Zhu, Hanmin Huang

引用次数: 0

Abstract

The incorporation of nitrogen-containing heterocycles by deconstruction of cycloamines with nucleophiles represents a powerful method in organic synthesis. However, this paradigm suffers severe challenges in the simultaneous construction of C-N and C-C bonds that are typically encountered in pharmaceuticals. Herein, a metal- and catalyst-free C-N and C-H bond activation reaction mediated by the haloarene-derived aryne intermediate is identified that enables the deconstructive dicarbofunctionalization of cyclic amines. With the facile method, a variety of amines can undergo the direct dicarbo-functionalization reaction with the highly accessible aryl halides and hydrocarbons, yielding N-arylpiperazines and functionalized arylamines with great potential as drug candidates.

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通过环胺与亲核物的解构掺入含氮杂环是有机合成中的一种有效方法。然而，这种方法在同时构建 C-N 和 C-C 键时面临严峻挑战，而这些键通常会在药物中遇到。在这里，我们发现了一种由卤代芳烃中间体介导的无金属、无催化剂的 C-N 和 C-H 键活化反应，该反应可实现环胺的解构二官能化。利用这种简便的方法，多种胺类可与高易得性芳基卤化物和烃类发生直接的二卡伯官能化反应，生成 N-芳基哌嗪和官能化芳基胺，具有作为候选药物的巨大潜力。

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 Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.