5 palladium on charcoal; hydrogen in ethanol T=20°C; 16 h;

hydrogen; platinum(IV) oxide in acetic acid 15 h; Heating;

1.1: hydrogenchloride / 1,4-dioxane; water / 1 h / 20 °C / |Inert atmosphere 1.2: 16 h / 20 °C / |Inert atmosphere 1.3: 6 h / 20 °C / |Inert atmosphere 2.1: lithium aluminium tetrahydride / diethyl ether / 0.75 h / 0 - 20 °C / |Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane; tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 4.1: hydrogenchloride; sodium tetrahydroborate / ethanol / 16 h / -15 °C / |Inert atmosphere 5.1: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 6.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 7.1: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme

1: lithium aluminium tetrahydride / diethyl ether / 0.75 h / 0 - 20 °C / |Inert atmosphere 2: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane; tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 3: hydrogenchloride; sodium tetrahydroborate / ethanol / 16 h / -15 °C / |Inert atmosphere 4: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 5: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 6: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme

1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane; tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 2: hydrogenchloride; sodium tetrahydroborate / ethanol / 16 h / -15 °C / |Inert atmosphere 3: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 4: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 5: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme

1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 5 h / 0 - 20 °C / |Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 2 h / -78 °C / |Inert atmosphere 2.2: 2.5 h / -78 °C / |Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane; water / 1 h / 20 °C / |Inert atmosphere 3.2: 16 h / 20 °C / |Inert atmosphere 3.3: 6 h / 20 °C / |Inert atmosphere 4.1: lithium aluminium tetrahydride / diethyl ether / 0.75 h / 0 - 20 °C / |Inert atmosphere 5.1: triphenylphosphine; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide / tetrahydrofuran / 12 h / -10 - 20 °C / |Inert atmosphere 6.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 - 20 °C / |Inert atmosphere 7.1: triethylamine; 1-propanephosphonic acid cyclic anhydride / ethyl acetate / 6 h / 20 °C / |Inert atmosphere 8.1: boron trifluoride diethyl etherate / dichloromethane / 36 h / 0 - 20 °C / |Inert atmosphere 9.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 10.1: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme

1.1: dichloromethane / 24 h / 20 °C / |Inert atmosphere 2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 2 h / -78 °C / |Inert atmosphere 2.2: 2.5 h / -78 °C / |Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane; water / 1 h / 20 °C / |Inert atmosphere 3.2: 16 h / 20 °C / |Inert atmosphere 3.3: 6 h / 20 °C / |Inert atmosphere 4.1: lithium aluminium tetrahydride / diethyl ether / 0.75 h / 0 - 20 °C / |Inert atmosphere 5.1: triphenylphosphine; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide / tetrahydrofuran / 12 h / -10 - 20 °C / |Inert atmosphere 6.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 - 20 °C / |Inert atmosphere 7.1: triethylamine; 1-propanephosphonic acid cyclic anhydride / ethyl acetate / 6 h / 20 °C / |Inert atmosphere 8.1: boron trifluoride diethyl etherate / dichloromethane / 36 h / 0 - 20 °C / |Inert atmosphere 9.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 10.1: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme

1.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 2 h / -78 °C / |Inert atmosphere 1.2: 2.5 h / -78 °C / |Inert atmosphere 2.1: hydrogenchloride / 1,4-dioxane; water / 1 h / 20 °C / |Inert atmosphere 2.2: 16 h / 20 °C / |Inert atmosphere 2.3: 6 h / 20 °C / |Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 0.75 h / 0 - 20 °C / |Inert atmosphere 4.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane; tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 5.1: hydrogenchloride; sodium tetrahydroborate / ethanol / 16 h / -15 °C / |Inert atmosphere 6.1: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 7.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 8.1: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme

1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane; tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 2: hydrogenchloride; sodium tetrahydroborate / ethanol / 16 h / -15 °C / |Inert atmosphere 3: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 4: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 5: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme

1: hydrogenchloride; sodium tetrahydroborate / ethanol / 16 h / -15 °C / |Inert atmosphere 2: trifluorormethanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 3: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / dichloromethane / 18 h / 40 °C / |Inert atmosphere 4: 5 palladium on charcoal; hydrogen / ethanol / 16 h / 20 °C View Scheme