Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy

Hui-Min Jiang; Jing-Hao Qin; Qing Sun; Dong Zhang; Jin-Peng Jiang; Xuan-Hui Ouyang; Ren-Jie Song; Jin-Heng Li

doi:10.1039/D2QO00706A

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Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy†

Hui-Min Jiang,^a Jing-Hao Qin,^a Qing Sun,

^a Dong Zhang,^a Jin-Peng Jiang,^a Xuan-Hui Ouyang,

*^a Ren-Jie Song

*^a and Jin-Heng Li

*^abc

Author affiliations

* Corresponding authors

^a Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
E-mail: xuanhuiouyang@163.com, srj0731@hnu.edu.cn, jhli@hnu.edu.cn

^b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

^c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 475004, China

Abstract

A copper-promoted reductive cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines for producing N-alkylbenzenamines is described. Using 4-alkyl-1,4-dihydropyridines as alkyl radical sources and internal reducing agents enables the construction of C(sp³)–N bonds under oxidative conditions, which provide an elegant complementary platform to assemble N-alkylbenzenamines with good tolerance for sensitive functional groups.

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Article information

DOI: https://doi.org/10.1039/D2QO00706A
Article type: Research Article
Submitted: 05 May 2022
Accepted: 16 Jun 2022
First published: 17 Jun 2022

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Org. Chem. Front., 2022,9, 4070-4077

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Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy

H. Jiang, J. Qin, Q. Sun, D. Zhang, J. Jiang, X. Ouyang, R. Song and J. Li, Org. Chem. Front., 2022, 9, 4070 DOI: 10.1039/D2QO00706A

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Organic Chemistry Frontiers

Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy†

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Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy

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