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

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.