CuCl2·2H2O/TBHP mediated synthesis of β-enaminones via coupling reaction of vinyl azides with aldehydes

Yaohong Zhang; Mengqiang Luo; Yichan Zhang; Kai Cheng; Yong Li; Chenze Qi; Runpu Shen; Hai Wang

doi:10.1039/D1OB02479E

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CuCl₂·2H₂O/TBHP mediated synthesis of β-enaminones via coupling reaction of vinyl azides with aldehydes†

Yaohong Zhang,

*^a Mengqiang Luo,^ab Yichan Zhang,^c Kai Cheng,

^a Yong Li,

^a Chenze Qi,^a Runpu Shen^b and Hai Wang*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, School of Life Science, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang, P. R. China
E-mail: wanghai@usx.edu.cn, zhangyhsxu@126.com

^b School of Chemistry and Chemical Engineering, Zhejiang Engineering Research Center of Fat-soluble Vitamin, Shaoxing University, Shaoxing, Zhejiang, P. R. China

^c Department of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng, Jiangsu, P. R. China

Abstract

A facile and efficient oxidative functionalization of vinyl azides with aldehydes furnishing a diverse array of β-acylated enaminones was developed. The cross coupling was accomplished in the presence of CuCl₂·2H₂O/TBHP and produced the desired β-acylated enaminones in a (Z)-stereo-selective and atom-economic manner, which make this protocol particularly attractive. In the transformation, the new C–C and C–N bonds were formed via a one-pot strategy including the process of radical addition and recombination.

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Article information

DOI: https://doi.org/10.1039/D1OB02479E
Article type: Paper
Submitted: 24 Dec 2021
Accepted: 04 Feb 2022
First published: 07 Feb 2022

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Org. Biomol. Chem., 2022,20, 1952-1957

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CuCl₂·2H₂O/TBHP mediated synthesis of β-enaminones via coupling reaction of vinyl azides with aldehydes

Y. Zhang, M. Luo, Y. Zhang, K. Cheng, Y. Li, C. Qi, R. Shen and H. Wang, Org. Biomol. Chem., 2022, 20, 1952 DOI: 10.1039/D1OB02479E

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Organic & Biomolecular Chemistry