Ce(OTf)₃-Catalyzed [3 + 2] Cycloaddition of Azides with Nitroolefins: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles

Ying-Chun Wang, Yu-Yang Xie, Hong-En Qu, Heng-Shan Wang*, Ying-Ming Pan* and Fu-Ping Huang

*School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004, People's Republic of China, Email: whengshan163.com, panym2013hotmail.com

Y.-C. Wang, Y.-Y. Xie, H.-E. Qu, H.-S. Wang, Y.-M. Pan, F.-P. Huang, J. Org. Chem., 2014, 79, 4463-4464.

DOI: 10.1021/jo5004339

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Abstract

A Ce(OTf)₃-catalyzed [3 + 2] cycloaddition of organic azides with nitroolefins and subsequent elimination reaction selectively produces 1,5-disubstituted 1,2,3-triazoles in very good yields. Both benzyl and phenyl azides react with a broad range of aryl nitroolefins containing a wide range of functionalities.

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Key Words

1,2,3-Triazoles

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ID: J42-Y2014