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Copper-Promoted One-Pot Sandmeyer-Type Reaction for the Synthesis of N-Aryltriazoles

Menghan Cui, Rong Wang, Qing Yang and Chunxiang Kuang*

*Shanghai Key Lab of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, Shanghai 200092, China, Email:

M. Cui, R. Wang, Q. Yang, C. Kuang, J. Org. Chem., 2022, 87, 9654-9662.

DOI: 10.1021/acs.joc.2c00697

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Diazonium salts, formed from aromatic amines and tert-butyl nitrite in the presence of fluoroboric acid, reacted with triazoles in a copper-catalyzed Sandmeyer-type reaction under mild conditions to afford N-aryltriazoles in good yields. This method is amenable to a wide range of aromatic amines and triazoles and shows diverse functional group tolerance.

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proposed mechanism

Key Words

Sandmeyer reaction, 1,2,3-triazoles, benzotriazoles, N-arylation

ID: J42-Y2022