t        BuOK/DMSO/O2 catalyzed direct α-C(sp3)–H alkylation with styrenes: productive α-amino radicals for hydroaminoalkylation

Zhangqiang Yan; Zhen Zhang; Tao Wen; Lihua Ye; Bo Jin; Chihong Zhang; Wenkun Wang; Zhong-Ning Chen; Hu Cai

doi:10.1039/D2QO01911F

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^tBuOK/DMSO/O₂ catalyzed direct α-C(sp³)–H alkylation with styrenes: productive α-amino radicals for hydroaminoalkylation†

Zhangqiang Yan,^a Zhen Zhang,*^a Tao Wen,^a Lihua Ye,^a Bo Jin,^a Chihong Zhang,^a Wenkun Wang,^a Zhong-Ning Chen

^ab and Hu Cai

*^a

Author affiliations

* Corresponding authors

^a College of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, Jiangxi Province, People's Republic of China
E-mail: caihu@ncu.edu.cn

^b Fujian Institute of Research on the Structure, Chinese Academy of Science, Fuzhou, Fujian 350002, People's Republic of China

Abstract

Direct α-C(sp³)–H alkylation of hydroaminoalkylation (HAA) catalyzed by ^tBuOK/DMSO/O₂ from α-aryl benzylamines with styrenes is reported. The reaction has delivered diverse selectively substituted amines and N-heterocycles under mild conditions. Mechanism studies have shown that α-aminoalkyl radicals act as intermediates and hydrogen atom transfer (HAT) plays a crucial role in the ^tBuOK/DMSO/O₂ system.

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Article information

DOI: https://doi.org/10.1039/D2QO01911F
Article type: Research Article
Submitted: 01 Dec 2022
Accepted: 01 May 2023
First published: 02 May 2023

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Org. Chem. Front., 2023,10, 2714-2720

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^tBuOK/DMSO/O₂ catalyzed direct α-C(sp³)–H alkylation with styrenes: productive α-amino radicals for hydroaminoalkylation

Z. Yan, Z. Zhang, T. Wen, L. Ye, B. Jin, C. Zhang, W. Wang, Z. Chen and H. Cai, Org. Chem. Front., 2023, 10, 2714 DOI: 10.1039/D2QO01911F

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