Three-component photoredox 1,2-alkylamination of styrenes with alkanes and nitrogen nucleophiles via C(sp3)–H bond cleavage

Jing Huang; Yun-Yan Liang; Xuan-Hui Ouyang; Yu-Ting Xiao; Jing-Hao Qin; Ren-Jie Song; Jin-Heng Li

doi:10.1039/D1QO01263K

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Three-component photoredox 1,2-alkylamination of styrenes with alkanes and nitrogen nucleophiles via C(sp³)–H bond cleavage†

Jing Huang,^a Yun-Yan Liang,^a Xuan-Hui Ouyang,*^a Yu-Ting Xiao,^a Jing-Hao Qin,^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 three-component photoredox 1,2-alkylamination of styrenes involving functionalization of C(sp³)–H bonds in alkyl halides instead of functionalization of C-halogen bonds is disclosed. A variety of commercialized C(sp³)–H alkanes, including dichloromethane, acetonitrile, and acetone, used as alkyl radical precursors and solvents, were compatible with this methodology. The mechanistic study shows that alkyl radicals are generated by hydrogen atom transfer (HAT) between aryl radicals and alkyl halides.

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Article information

DOI: https://doi.org/10.1039/D1QO01263K
Article type: Research Article
Submitted: 23 Aug 2021
Accepted: 29 Oct 2021
First published: 03 Nov 2021

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Org. Chem. Front., 2021,8, 7009-7014

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Three-component photoredox 1,2-alkylamination of styrenes with alkanes and nitrogen nucleophiles via C(sp³)–H bond cleavage

J. Huang, Y. Liang, X. Ouyang, Y. Xiao, J. Qin, R. Song and J. Li, Org. Chem. Front., 2021, 8, 7009 DOI: 10.1039/D1QO01263K

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