(methylation);

palladium 10 on activated carbon in 1,2-dichloro-benzene T=180°C;

sodium hydroxide in methanol; water; benzene 2.5 h; Irradiation;

1: 84 percent / benzene / 1 h / Heating 2: 58 percent / NaBH4 / dimethylformamide / 1 h / 110 °C 3: 29 percent / NaOH / benzene; H2O; methanol / 2.5 h / Irradiation View Scheme

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 3: sodium acetate / ethanol / 1 h / 80 °C 4: 1,2-dichloro-benzene / 4 h / Inert atmosphere; Heating; Microwave irradiation 5: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C View Scheme

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 2: sodium acetate / ethanol / 1 h / 80 °C 3: 1,2-dichloro-benzene / 4 h / Inert atmosphere; Heating; Microwave irradiation 4: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C View Scheme

1.1: bis-triphenylphosphine-palladium(II) chloride; 1,1'-bis-(diphenylphosphino)ferrocene; lithium chloride / N,N-dimethyl-formamide / 2 h / 180 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 1 h / 50 °C / Inert atmosphere 3.1: borane-THF / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.2: 1 h / 50 °C 4.1: pyridinium chlorochromate / 1.5 h / 20 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 5.2: 4 h / -78 - 20 °C / Inert atmosphere 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 1 h / 80 °C 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; N,N-dimethyl-formamide / 0.5 h / 80 °C / Inert atmosphere 8.1: sodium acetate / ethanol / 1 h / 80 °C 9.1: 1,2-dichloro-benzene / 4 h / Inert atmosphere; Heating; Microwave irradiation 10.1: 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 / 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

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

1: sodium acetate / ethanol / 1 h / 80 °C 2: 1,2-dichloro-benzene / 4 h / Inert atmosphere; Heating; Microwave irradiation 3: palladium 10 on activated carbon / 1,2-dichloro-benzene / 180 °C View Scheme