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Regioselective Synthesis of N2-Aryl 1,2,3-Triazoles via Electro-oxidative Coupling of Enamines and Aryldiazonium Salts.

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An efficient synthetic route for the construction of N2-aryl 1,2,3-triazoles is reported via sequential C-N bond formation and electro-oxidative N-N coupling under metal-free conditions. Readily accessible 2-aminoacrylates and aryldiazonium salts… Click to show full abstract

An efficient synthetic route for the construction of N2-aryl 1,2,3-triazoles is reported via sequential C-N bond formation and electro-oxidative N-N coupling under metal-free conditions. Readily accessible 2-aminoacrylates and aryldiazonium salts were used as starting materials, and the developed protocol displays excellent functional group tolerance, allowing an extensive range of substrate scope up to 91% isolated yield. Various mechanistic studies, along with the isolation of an intermediate adduct, refer to successive ionic and radical reaction sequences.

Keywords: aryldiazonium salts; electro oxidative; aryl triazoles; oxidative coupling

Journal Title: Organic letters
Year Published: 2022

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