1.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere 2.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.2: 1 h / 50 °C 3.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 4 h / -78 - 20 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 7.1: sodium acetate / ethanol / 1 h / 80 °C 8.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 9.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 10.1: 12 h / 20 °C 10.2: 0.5 h / 20 °C 11.1: Jone's reagent / acetone / 0.5 h / 0 °C 11.2: Cooling with ice View Scheme

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

1.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere 2.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.2: 1 h / 50 °C 3.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 4 h / -78 - 20 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 7.1: sodium acetate / ethanol / 1 h / 80 °C 8.1: 1,2-dichloro-benzene / 1 h / Inert atmosphere; Heating; Microwave irradiation 9.1: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C 10.1: 12 h / 20 °C 10.2: 0.5 h / 20 °C View Scheme

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

Multi-step reaction with 5 steps 1.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere2.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere2.2: 1 h / 50 °C3.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere4.2: 4 h / -78 - 20 °C / Inert atmosphere5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C  

Multi-step reaction with 2 steps 1.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere2.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere2.2: 1 h / 50 °C  

Multi-step reaction with 4 steps 1.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere2.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere2.2: 1 h / 50 °C3.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere4.2: 4 h / -78 - 20 °C / Inert atmosphere  

Multi-step reaction with 7 steps 1.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere2.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere2.2: 1 h / 50 °C3.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere4.2: 4 h / -78 - 20 °C / Inert atmosphere5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C6.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere7.1: sodium acetate / ethanol / 1 h / 80 °C  

Multi-step reaction with 7 steps 1.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere2.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere2.2: 1 h / 50 °C3.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere4.2: 4 h / -78 - 20 °C / Inert atmosphere5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere7.1: sodium acetate / ethanol / 1 h / 80 °C