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  • Title: Synthesis of bicyclic imidazoles via [2 + 3] cycloaddition between nitriles and regioselectively generated α-imino gold carbene intermediates.
    Author: Xiao Y, Zhang L.
    Journal: Org Lett; 2012 Sep 07; 14(17):4662-5. PubMed ID: 22917160.
    Abstract:
    The cyclic α-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl(3) as the catalyst.
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