1.1: diethyl ether / 5 h / 0 - 20 °C 1.2: 5 h / 0 - 20 °C 2.1: methanol / 4 h / |Reflux 3.1: sodium tetrahydroborate / tetrahydrofuran / 6 h / 0 - 20 °C View Scheme

nitrogen; Pd(PPh3)4; palladium in water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile

1.1: triethylamine; palladium diacetate; lithium chloride; 1,1'-bis-(diphenylphosphino)ferrocene; triethyl borane / hexane; tetrahydrofuran / 8 h / 50 °C / |Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C / |Inert atmosphere 2.2: 1 h / 0 - 20 °C / |Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / |Inert atmosphere 4.1: dichloromethane / 1 h / 20 °C / |Inert atmosphere 5.1: triethylamine; methanol / dichloromethane / 4 h / 20 °C / |Inert atmosphere 6.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 1.17 h / -78 - 0 °C / |Inert atmosphere 7.1: dichloromethane / 2 h / 20 °C / |Inert atmosphere 8.1: zinc; acetic acid / 2.08 h / 0 - 20 °C / |Inert atmosphere 9.1: acetic acid; sodium cyanoborohydride / ethanol / |Reflux; |Inert atmosphere 10.1: sodium hydrogencarbonate / dichloromethane; water / 20 °C 11.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / |Reflux; |Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere 13.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere 14.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere 15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 16.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere 17.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C 18.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere 19.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 20.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 20.2: 0.5 h / 50 °C / |Inert atmosphere 21.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

in hexane; N,N-dimethyl-formamide

diethyl ether; ammonia; sodium amide

in water; acetic acid 48 h; Ambient temperature;

sodium hydride in tetrahydrofuran T=0 - 20°C;