On the involvement of NHC carbenes in catalytic reactions by iridium complexes, nanoparticle and bulk metal dispersed in imidazolium ionic liquids

D/H exchange reactions at C2, C4 and C5 of the imidazolium cation were observed in catalytic hydrogenation reactions promoted by classical Ir(I) colloid precursors and [Ir(0)](n) nanoparticles dispersed in deuterated imidazolium ionic liquids indicating the participation of carbene species in this media. However, no D/H exchange reaction was observed in cyclohexene hydrogenation promoted by iridium bulk metal dispersed in the ionic liquid [BMI]-d(3).NTf(2). The D/H labeling experiments suggest that the ionic liquids interact with the metal centers preferentially as aggregates rather than isolated ions.