Electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles

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. 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, alpha-thio, alpha-amino acid derivatives as well as alpha-amino, beta-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.

Automated summary

By electrochemical oxidative difunctionalization, the authors achieved functionalization of diazo compounds with two different nucleophiles. This method allows the synthesis of structurally diverse heteroatom-containing compounds, which are difficult to access by traditional methods, and display important synthetic applications. The reaction conditions are mild, exhibiting excellent functional group tolerance and efficiency for large-scale synthesis.