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

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

doi:10.1039/D4QO00623B

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

Weijie Yu,‡^a Hongjie Zhang,‡^a Zhipeng Shen,^a Lingyun Yang,^a Jin Luo,

*^b Wendong Li,^a Kuang Zhao,^a Xiaolong Li,^a Jiale Xu,^a Yuan Zhou*^a and Tao Wang

*^a

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* Corresponding authors

^a National Research Center for Carbohydrate Synthesis, Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education and Jiangxi Province Key Laboratory of Chemical Biology, Jiangxi Normal University, Nanchang 330022, Jiangxi, P. R. China
E-mail: zhouy@jxnu.edu.cn, wangtao@jxnu.edu.cn

^b Analytical and Testing Center, Jiangxi Normal University, Nanchang, Jiangxi, P. R. China
E-mail: Jinluo@jxnu.edu.cn

Abstract

An electroreduction-enabled aryl-to-alkyl radical relay arylation reaction of the remote C(sp³)–H bond of 2-iodoalkylarenes is reported. This electrochemical strategy takes place via 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.

Organic Chemistry Frontiers

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

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

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