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 13.1: Jone's reagent / acetone / 0.5 h / 0 °C 13.2: Cooling with ice View Scheme

potassium carbonate in acetone 29 h; Heating;

potassium carbonate; acetone

1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C 3: 95 percent / K2CO3 / acetone / Heating 4: 87 percent / Na-Hg / methanol; ethyl acetate / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h 6: 73 percent / KI, K2CO3 / acetone / 48 h / 60 °C 7: 85 percent / H2O2, H2SO4 / CH2Cl2 / 0.17 h 8: 97 percent / imidazole, DMAP / CH2Cl2 9: 95 percent / quinoline / 10percent Pd/CaCO3 / ethyl acetate 10: 95 percent / toluene / 2 h / 100 °C 11: 1.) L-Selectride, 2.) DMAP / 1.) THF 12: 65 percent / DBU / 1 h / Ambient temperature 13: 50 percent / 4 h / 200 °C View Scheme

1: 90 percent / LiBr / tetrahydrofuran / 12 h 2: 73 percent / KI, K2CO3 / acetone / 48 h / 60 °C 3: 85 percent / H2O2, H2SO4 / CH2Cl2 / 0.17 h 4: 97 percent / imidazole, DMAP / CH2Cl2 5: 95 percent / quinoline / 10percent Pd/CaCO3 / ethyl acetate 6: 95 percent / toluene / 2 h / 100 °C 7: 1.) L-Selectride, 2.) DMAP / 1.) THF 8: 65 percent / DBU / 1 h / Ambient temperature 9: 50 percent / 4 h / 200 °C View Scheme

1: 95 percent / quinoline / 10percent Pd/CaCO3 / ethyl acetate 2: 95 percent / toluene / 2 h / 100 °C 3: 1.) L-Selectride, 2.) DMAP / 1.) THF 4: 65 percent / DBU / 1 h / Ambient temperature 5: 50 percent / 4 h / 200 °C View Scheme

1: 92 percent / K2CO3 / acetone / Heating 2: 91 percent / N,N-dimethyl-aniline / Heating View Scheme

T=200°C; 4 h;

1: 95 percent / toluene / 2 h / 100 °C 2: 1.) L-Selectride, 2.) DMAP / 1.) THF 3: 65 percent / DBU / 1 h / Ambient temperature 4: 50 percent / 4 h / 200 °C View Scheme

N,N-dimethyl-aniline