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A cationic NHC 1+ bearing an N-bound 2,3-bis(diisopropylamino)cyclopropenium group is reported. From an easily available dicationic imidazolium precursor, the coordination abilities and stereo-electronic properties of 1+ are evaluated by the formation of Pd(ii), Rh(i) and Au(i) complexes. The cationic gold(i) complex is implemented in representative intramolecular Au(i)-catalyzed cyclizations.

N-Cyclopropenio-imidazol-2-ylidene: An N-heterocyclic carbene bearing an N-cationic substituent