tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; Inert atmosphere;

N-bromosuccinmide in tetrahydrofuran; water T=0°C; 1.75 h;

[2,2']bipyridinyl; copper; zinc; molybdenum hexacarbonate in 1,4-dioxane 115 h; Heating; Yield given. Further byproducts given. Yields of byproduct given;

zinc; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; methanol 2.5 h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; Inert atmosphere;

1.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 3.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / |Inert atmosphere 4.1: N,N-dimethyl-formamide / 18 h / 20 °C / |Darkness 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 5.2: -78 - 20 °C 6.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 7.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere; |Cooling with acetone-dry ice 8.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / |Inert atmosphere; |Cooling with acetone-dry ice 9.1: Pd(1,2-bis(diphenylphosphino)ethane)Cl2 / tetrahydrofuran / 0.08 h / 0 °C / |Cooling with acetone-dry ice; |Inert atmosphere 9.2: 4.5 h / 0 °C / |Inert atmosphere 10.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme

1: H2 / PtO2 2: OH(1-) / Heating 4: 400 °C View Scheme

1: 37 percent / SeO2, t-BuOOH / CH2Cl2 / 2 h / Ambient temperature 2: 100 percent / Ph3P, I2, imidazole / diethyl ether; acetonitrile / 0.5 h / Ambient temperature 3: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 4: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 5: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1.1: NBS / tetrahydrofuran; H2O 1.2: 62 percent / K2CO3 / methanol 2.1: 78 percent / NaIO4; aq. HCl / tetrahydrofuran / 4 h / 20 °C View Scheme

1.1: AD-mix-β 1.2: MeSO2Cl; pyridine 2.1: Mn; 2,5,6-collidine; Me3SiCl / Cp2TiCl2 / tetrahydrofuran / 2 h / 20 °C 2.2: 47 percent / Bu4NF / tetrahydrofuran / 3 h 3.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C 4.1: 98 percent / K2CO3 / methanol / 2 h 5.1: PCC / CH2Cl2 / 1 h / 20 °C 6.1: K2CO3 / methanol / 1.5 h / 20 °C 7.1: 550 mg / LiAlH4 / diethyl ether / 3 h / 0 °C 8.1: CBr4; PPh3 / benzene / 2 h / 0 °C 9.1: 75 percent / Mn / Cp2TiCl2 / tetrahydrofuran / 20 °C 10.1: 90 percent / TBAF / tetrahydrofuran / 11 h / 60 °C View Scheme