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Electrochemical Difunctionalization of Alkenes towards the Synthesis of β-Bromoethers under Metal-Free Conditions

Zhengjiang Fu*, Feiwu Chen, Guangguo Hao, Xuezheng Yi, Junhua Zeng , Hu Cai*

*School of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, China, Email: fuzhengjiangncu.edu.cn, caihuncu.edu.cn

F. Luo, X. Chen, J. Yu, Y. Yin, X. Hu, Y. Hu, X. Liu, X. Chen, S. Zhang, Y. Hu, Synthesis, 2023, 55, 1451-1459.

DOI: 10.1055/a-2025-1822


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Abstract

A metal-free electrochemical vicinal difunctionalization of various alkenes with dibromomethane in alcohol as solvent provides β-bromo-α-alkyloxyalkanes with good functional group tolerance under ambient conditions. Preliminary mechanistic studies indicate the oxidation of bromine source occurs prior to that of alkene substrate with the involvement of bromine radical during electrolysis.


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Key Words

multicomponent reactions, alkenes, β-bromoethers, ethers, bromides, electrochemistry, metal-free conditions


ID: J66-Y2023