hydrogen; [Rh(1,3-dimesitylimidazole-2-ylidene)(cod)Cl] in toluene T=125°C; 24 h;

hydrogen; platinum(IV) oxide in methanol T=120°C; P=45600 Torr; 24 h; Yield given;

1: benzene / 3 h / Heating 2: H2 / 10 percent Pd/C / methanol / 12 h / 20 °C View Scheme

1: tetrahydrofuran / 2.5 h / 0 °C 2: benzene / 3 h / Heating 3: H2 / 10 percent Pd/C / methanol / 12 h / 20 °C View Scheme

1: tetrahydrofuran / 2.5 h / 0 °C 2: benzene / 3 h / Heating 3: H2 / 10 percent Pd/C / methanol / 12 h / 20 °C View Scheme

1.1: Mg / tetrahydrofuran / 1 h / Heating 1.2: 80 percent / tetrahydrofuran / 0 °C 2.1: tetrahydrofuran / 2.5 h / 0 °C 3.1: benzene / 3 h / Heating 4.1: H2 / 10 percent Pd/C / methanol / 12 h / 20 °C View Scheme

1: water; potassium hydroxide / methanol / 3 h / |Reflux 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 36 h / 20 °C 3: AlCl3, aluminium chloride; lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 60 °C / |Inert atmosphere View Scheme

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 36 h / 20 °C 2: AlCl3, aluminium chloride; lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 60 °C / |Inert atmosphere View Scheme

lithium 1.) THF, 2.) THF, 0 deg C, 12 h; Yield given. Multistep reaction;