In a quest of redox-switchable metathesis catalysts we attempted synthesis of ruthenium quinonylidene complexes using two synthetic pathways. First, Hoveyda-type complexes bearing chelating benzylidene and naphthylidene ligands substituted with two alkoxy/hydroxy groups were synthesized and characterized. The catalysts were tested in model ring-closing metathesis reactions, and displayed interesting correlations between structure and catalytic activity. Unfortunately, numerous attempts at oxidation of the complexes to derivatives of benzo-and naphthoquinone were unsuccessful. However, the second approach, using exchange reaction of ruthenium precursor with vinylquinone ligand, gave a transient unstable product observed with 1 H NMR. The experimental data suggest that conjugation of electron-deficient quinones to the ruthenium centre results in intrinsically unstable species, which undergo secondary reactions under ambient conditions.