Ce (OTf) 3-catalyzed [3+ 2] cycloaddition of azides with nitroolefins: Regioselective synthesis of 1, 5-disubstituted 1, 2, 3-triazoles

…, HE Qu, HS Wang, YM Pan, FP Huang

Index: Wang, Ying-Chun; Xie, Yu-Yang; Qu, Hong-En; Wang, Heng-Shan; Pan, Ying-Ming; Huang, Fu-Ping Journal of Organic Chemistry, 2014 , vol. 79, # 10 p. 4463 - 4469

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Citation Number: 42

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.