Electrochemical Oxidative One-Pot Difunctionalization of Diazo Compounds with Triazoles and Nucleophiles

Abstract

Carbene radical coupling reactions are rarely developed due to their high reactivity. Here, we present a distinct electrochemical one-pot difunctionalization of diazo compounds with triazoles and nucleophiles. This method represents an effective strategy to access to fully-substituted triazole derivatives which can’t be accessible using the known methods. This transformation exhibits synthetically useful yields and high regioselectivity, without the need for external chemical oxidants or metal catalysts. Furthermore, a variety of nucleophiles can be employed in this reaction to construct quaternary Csp3-N and Csp3-X (X = O/F) bonds. The reaction mechanism investigations show that this unprecedent pathway was promoted via a carbene radical coupling process followed by further oxidation and nucleophilic addition.