Aryl-to-alkyl radical relay arylation reaction of remote C(sp3)-H bond using 1,4-dicyanobenzene as an electrochemical redox-mediator

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-06-07 DOI:10.1039/d4qo00623b

Weijie Yu, Hongjie Zhang, Zhipeng Shen, Lingyun Yang, Jin Luo, Wendong Li, Kuang Zhao, Xiaolong Li, Jiale Xu, Yuan Zhou, Tao Wang

引用次数: 0

Abstract

An electroreduction-enabled aryl-to-alkyl radical relay arylation reaction of remote C(sp3)-H bond of 2-iodoalkylarenes is reported. This electrochemical strategy undergoes a 1,5-H transfer process, leading to various arylated products bearing all-carbon quaternary centers under transition-metal and ligand-free conditions. The aryl nitriles serve as both aryl radical precursors and redox mediators in this transformation.

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以 1,4-二氰基苯为电化学氧化还原介质实现远端 C（sp3）-H 键的芳基-烷基自由基中继芳基化反应

本研究报道了一种电还原催化的 2-iodoalkylarenes 远端 C(sp3)-H 键的芳基-烷基自由基接替芳基化反应。这种电化学策略经历了一个 1,5-H 转移过程，在过渡金属和无配体条件下产生了各种带有全碳季中心的芳基化产物。在这一转化过程中，芳基腈既是芳基自由基前体，又是氧化还原媒介。

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.