in diethyl ether T=20 - 30°C; 1 h; Irradiationother solvent, other temperature, without irradiation; Product distribution;

hydrogenchloride 12 h; Ambient temperature;

1.1: pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 2.1: bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene; lithium chloride / N,N-dimethyl-formamide / 2 h / 180 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere 4.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.2: 1 h / 50 °C 5.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 6.2: 4 h / -78 - 20 °C / Inert atmosphere 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 8.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 9.1: sodium acetate / ethanol / 1 h / 80 °C 10.1: 1,2-dichloro-benzene / 2.5 h / Inert atmosphere; Heating; Microwave irradiation 11.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C View Scheme

1.1: pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 2.1: bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene; lithium chloride / N,N-dimethyl-formamide / 2 h / 180 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere 4.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.2: 1 h / 50 °C 5.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 6.2: 4 h / -78 - 20 °C / Inert atmosphere 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 8.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 9.1: sodium acetate / ethanol / 1 h / 80 °C 10.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 11.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 12.1: 12 h / 20 °C 12.2: 0.5 h / 20 °C View Scheme

1: potassium tert-butylate / dimethyl sulfoxide / 1.5 h / 100 °C / Inert atmosphere 2: oxygen; 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxy / benzene / 4 h / 70 °C View Scheme

1: 96 percent / potassium tert-butoxide / tetrahydrofuran / 12 h / 20 °C 2: 93 percent / triethylamine / CH2Cl2 / 3 h / 20 °C 3: 83 percent / Grubbs' second generation catalyst / CH2Cl2 / 24 h / Heating View Scheme

1.1: pyridine / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 2.1: bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene; lithium chloride / N,N-dimethyl-formamide / 2 h / 180 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere 4.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.2: 1 h / 50 °C 5.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 6.2: 4 h / -78 - 20 °C / Inert atmosphere 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 8.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 9.1: sodium acetate / ethanol / 1 h / 80 °C 10.1: 1,2-dichloro-benzene / 4 h / Inert atmosphere; Heating; Microwave irradiation 11.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C View Scheme