bis-triphenylphosphine-palladium(II) chloride; ethylmagnesium bromide 1.) Et2O, -20 deg C, 20 min, 2.) -20 deg C, 1.5 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

bis(acetylacetonate)nickel(II); ethylmagnesium bromide 1.) Et2O, -20 deg C, 20 min, 2.) -20 deg C, 1.5 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

1: Na / methanol / (electrolysis) 2: dimethylformamide 3: H2, NH3 / Raney-Co / methanol 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

lithium aluminium tetrahydride; diethyl ether

Cu2Cl2; ethylmagnesium bromide; n-octylmagnesium bromide in diethyl ether T=-20°C; 1.) 20 min, 2.) 1.5 h; Further byproducts given. Title compound not separated from byproducts;

bis-triphenylphosphine-palladium(II) chloride; ethylmagnesium bromide 1.) Et2O, -20 deg C, 20 min, 2.) -20 deg C, 1.5 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

bis(acetylacetonate)nickel(II); ethylmagnesium bromide 1.) Et2O, -20 deg C, 20 min, 2.) -20 deg C, 1.5 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

lead(IV) acetate; ammonium chloride T=20°C; 48 h;

1: Na / methanol / (electrolysis) 2: dimethylformamide View Scheme