1.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 1 h / 50 °C 2.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: 4 h / -78 - 20 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 6.1: sodium acetate / ethanol / 1 h / 80 °C 7.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 8.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 9.1: 12 h / 20 °C 9.2: 0.5 h / 20 °C 10.1: Jone's reagent / acetone / 0.5 h / 0 °C 10.2: Cooling with ice View Scheme

1.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 1 h / 50 °C 2.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: 4 h / -78 - 20 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 6.1: sodium acetate / ethanol / 1 h / 80 °C 7.1: 1,2-dichloro-benzene / 2.5 h / Inert atmosphere; Heating; Microwave irradiation 8.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C View Scheme

1.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 1 h / 50 °C 2.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: 4 h / -78 - 20 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 6.1: sodium acetate / ethanol / 1 h / 80 °C 7.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 8.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 9.1: 12 h / 20 °C 9.2: 0.5 h / 20 °C View Scheme

1.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 1 h / 50 °C 2.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: 4 h / -78 - 20 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 6.1: sodium acetate / ethanol / 1 h / 80 °C 7.1: 1,2-dichloro-benzene / 4 h / Inert atmosphere; Heating; Microwave irradiation 8.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C View Scheme

With  RuCl2(tricyclohexylphosphine)2(benzylidene) in  dichloromethane T=50°C; 1 h;   

With  potassium carbonate in  acetone  Ambient temperature;   

Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene; lithium chloride / N,N-dimethyl-formamide / 2 h / 180 °C / Inert atmosphere1.2: 2 h / 20 °C2.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere  

Multi-step reaction with 4 steps 1.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere1.2: 1 h / 50 °C2.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere3.2: 4 h / -78 - 20 °C / Inert atmosphere4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C  

Stage #1: With  borane in  tetrahydrofuran T=0°C; 1 h; Stage #2: With  sodium hydroxide; dihydrogen peroxide in  water T=50°C; 1 h;   

Multi-step reaction with 3 steps 1.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere1.2: 1 h / 50 °C2.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere3.2: 4 h / -78 - 20 °C / Inert atmosphere