Electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles

Dongfeng Yang, Zhipeng Guan, Yanan Peng, Shuxiang Zhu, Pengjie Wang, Zhiliang Huang, Hesham Alhumade, Dong Gu (), Hong Yi () and Aiwen Lei ()
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Dongfeng Yang: Wuhan University
Zhipeng Guan: Wuhan University
Yanan Peng: Wuhan University
Shuxiang Zhu: Wuhan University
Pengjie Wang: Wuhan University
Zhiliang Huang: Wuhan University
Hesham Alhumade: King Abdulaziz University
Dong Gu: Wuhan University
Hong Yi: Wuhan University
Aiwen Lei: Wuhan University

Nature Communications, 2023, vol. 14, issue 1, 1-8

Abstract: Abstract With the fast development of synthetic chemistry, the introduction of functional group into organic molecules has attracted increasing attention. In these reactions, the difunctionalization of unsaturated bonds, traditionally with one nucleophile and one electrophile, is a powerful strategy for the chemical synthesis. In this work, we develop a different path of electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles. Under metal-free and external oxidant-free conditions, a series of structurally diverse heteroatom-containing compounds hardly synthesized by traditional methods (such as high-value alkoxy-substituted phenylthioacetates, α-thio, α-amino acid derivatives as well as α-amino, β-amino acid derivatives) are obtained in synthetically useful yields. In addition, the procedure exhibits mild reaction conditions, excellent functional-group tolerance and good efficiency on large-scale synthesis. Importantly, the protocol is also amenable to the key intermediate of bioactive molecules in a simple and practical process.

Date: 2023
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DOI: 10.1038/s41467-023-37032-8

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