The synthesis and characterization of original NHC ligands based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) scaffold functionalized with a flanking barbituric heterocycle is described as well as their use as tunable ligands for efficient gold-catalyzed C-N, C-O, and C-C bond formations. High activity, regio-, chemo-, and stereoselectivities are obtained for hydroelementation and domino processes, underlining the excellent performance (TONs and TOFs) of these IPy-based ligands in gold catalysis. The gold-catalyzed domino reactions of 1,6-enynes give rise to functionalized heterocycles in excellent isolated yields under mild conditions. The efficiency of the NHC gold 5 complex is remarkable and mostly arises from a combination of steric protection and stabilization of the cationic Au active species by ligand 1 .
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