Metal-free electrochemical [3 + 2] heteroannulation of anilines with pyridines enabled by dual C–H radical aminations†

IF 9.2 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Green Chemistry Pub Date : 2021-10-12 DOI:10.1039/D1GC02922C

Mu-Jia Luo, Xuan-Hui Ouyang, Yan-Ping Zhu, Yang Li and Jin-Heng Li

引用次数: 1

Abstract

An unprecedented metal-/external-oxidant-free electrochemical intermolecular [3 + 2] heteroannulation of anilines with electron-deficient pyridines enabled by dual C–H radical aminations for producing functionally diverse benzo[4,5]imidazo[1,2-a]pyridines is described. The site-selectivity of aminations of aryl C(sp²)–H bonds relies on the electronic effect of two reaction partners: each contributed two reactive sites (a C(sp²)–H bond and a nitrogen atom-based functional group) and the electron-withdrawing groups at the 4 position of the pyridine ring are crucial. Mechanistic studies show that this method sequence consists of the generation of the nitrogen-centered radical (NCR) and the pyridine radical anion, radical coupling and dual C–N aminations.

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双C-H自由基胺化使苯胺与吡啶的电化学[3 + 2]非金属杂环化

描述了一种前所未有的无金属/无外部氧化剂的苯胺与缺电子吡啶的电化学分子间[3 + 2]杂环反应，通过双C-H自由基胺化产生功能多样的苯并[4,5]咪唑[1,2-a]吡啶。芳基C(sp2) -H键胺化的位点选择性取决于两个反应伙伴的电子效应:每个反应伙伴贡献两个反应位点(一个C(sp2) -H键和一个氮原子基官能团)，吡啶环4位的吸电子基团至关重要。机理研究表明，该方法序列由氮中心自由基(NCR)和吡啶自由基阴离子的生成、自由基偶联和双C-N胺化组成。

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

Green Chemistry 化学-化学综合

CiteScore

16.10

自引率

7.10%

发文量

677

审稿时长

1.4 months

期刊介绍： Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.