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- Title
Electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles.
- Authors
Yang, Dongfeng; Guan, Zhipeng; Peng, Yanan; Zhu, Shuxiang; Wang, Pengjie; Huang, Zhiliang; Alhumade, Hesham; Gu, Dong; Yi, Hong; Lei, Aiwen
- 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. The difunctionalization of diazo compounds, traditionally with one nucleophile and one electrophile, is a powerful strategy. Here, the authors develop a path of electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles.
- Subjects
NUCLEOPHILES; CHEMICAL synthesis; ACID derivatives; FUNCTIONAL groups; DIAZO compounds
- Publication
Nature Communications, 2023, Vol 14, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-023-37032-8