Synthesis of Bicyclic Imidazoles via [2+ 3] Cycloaddition between Nitriles and Regioselectively Generated α-Imino Gold Carbene Intermediates
Y Xiao, L Zhang
Index: Xiao, Yuanjing; Zhang, Liming Organic Letters, 2012 , vol. 14, # 17 p. 4662 - 4665
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Citation Number: 46
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] ...
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