A complete series of ten Au(I) and Au(III) NHC complexes of the general formulas [Au I X( i Pr 2 -bimy)] (1−3, X = Cl, Br, and I), [Au I ( i Pr 2 -bimy) 2 ]BF 4 (4), [Au III X 3 ( i Pr 2 -bimy)] (5−7, X = Cl, Br, and I) and trans-[Au III X 2 ( i Pr 2 -bimy)]BF 4 (8−10, X = Cl, Br, and I) bearing the i Pr 2 -bimy ligand, and all three common halido ligands have been synthesized and fully characterized. Detailed trends in their NMR and UV−Vis spectroscopic properties have been studied, and their electrochemical behavior have been probed by cyclic voltammetry. The solid state molecular structures of all new complexes determined by single crystal X-ray diffraction are also described.

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A systematic evaluation of N-heterocyclic carbene ligands in the iron-catalyzed cross-coupling reactions of aryl chlorides and arylmagnesium reagents is performed. There is no clear correlation between the donor strength of the N-heterocyclic carbene and the reaction outcome. Instead, the highest yields of the desired biaryl product are obtained with sterically demanding ligands possessing large %V bur values. Through this study, SIPrNap has been identified as an efficient and general ligand for the coupling of both aryl chlorides and tosylates.

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