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J Org Chem. 2014 May 16;79(10):4463-9. doi: 10.1021/jo5004339. Epub 2014 Apr 25.

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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  • 1Key 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.

Abstract

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.

PMID:
24742349
[PubMed - indexed for MEDLINE]
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