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

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† Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004, People’s Republic of China
‡ College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People’s Republic of China
*E-mail: [email protected]. Phone: +86-773-5846279. Fax: +86-773-5803930 (H.-S.W.).
*E-mail: [email protected] (Y.-M.P.).
Cite this: J. Org. Chem. 2014, 79, 10, 4463–4469
Publication Date (Web):April 17, 2014
https://doi.org/10.1021/jo5004339
Copyright © 2014 American Chemical Society
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    Abstract

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    The first example of rare earth metal-catalyzed [3 + 2] cycloaddition of organic azides with nitroolefins and subsequent elimination reaction is described. In the presence of a catalytic amount of Ce(OTf)3, both benzyl and phenyl azides react with a broad range of aryl nitroolefins containing a range of functionalities selectively producing 1,5-disubstituted 1,2,3-triazoles in good to excellent yields.

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    General experimental methods; 1H and 13C NMR spectra of compounds 2a–2x and 3a–3c; high-resolution mass spectra of compounds 2a–2x and 3a–3c; and X-ray crystallographic files (CIF) for 2n and 3b. This material is available free of charge via the Internet at http://pubs.acs.org.

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