{"title":"Deconstructive Dicarbofunctionalization of Cyclic Amines Enabled by C-H and C-N Bond Activation","authors":"Qiming Zhu, Kaifang Wang, Yuyuan Fan, Tianze Zhang, Xianchen Song, Shuang Luo, Qiang Zhu, Hanmin Huang","doi":"10.1039/d5qo00270b","DOIUrl":null,"url":null,"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.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"214 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5qo00270b","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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.
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.
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