The synthesis and characterization of three novel trifluoromethylamido-containing boomerang precatalysts bearing various N-heterocyclic carbene (NHC) ligands are reported. Comparative kinetic and stability studies show the significant effect of the NHC on the catalyst reaction profile. An investigation of the reaction scope for diverse metathesis transformations has allowed us to establish the influence of the NHC on catalyst activity, especially as a function of substrate steric bulk. The excellent stability of one of the novel precatalysts is disclosed, and allowed for its recovery at the end of catalytic reactions. Large-scale ring-closing metathesis, enyne-metathesis and cross-metathesis experiments have revealed the recoverability of the catalyst. ICP-MS analyses of the synthesized products reveal Ru contamination levels of less than 2.5 ppm.