dimethylsulfide borane complex in tetrahydrofuran T=0 - 20°C; 6 h;

sodium methylate in methanol Heating;

1: glycerin; sulfuric acid; nitrobenzene / 5 h / 130 °C 2: 1.60 g / Br2 / acetic acid / 12 h / 80 °C 3: 85 percent / (tol)3P; triethylamine / Pd(OAc)2 / acetonitrile / 16 h / 120 °C 4: 87 percent / H2 / Pd/C / ethanol 5: 74 percent / AlCl3; LiAlH4 / tetrahydrofuran / 20 h / Heating View Scheme

1: 85 percent / (tol)3P; triethylamine / Pd(OAc)2 / acetonitrile / 16 h / 120 °C 2: 87 percent / H2 / Pd/C / ethanol 3: 74 percent / AlCl3; LiAlH4 / tetrahydrofuran / 20 h / Heating View Scheme

1: 78 percent / triethylamine; tri(o-tolyl)phosphane / palladium(II) acetate / dimethylformamide / 48 h / 140 °C 2: 52 percent / hydrogen / Pd/C / ethanol; ethyl acetate / 5 h / 20 °C / 760.05 Torr 3: 81 percent / dimethylformamide / 8 h / 140 °C 4: 90 percent / BH3*SMe2 / tetrahydrofuran / 2 h / 0 °C 5: 80 percent / BH3*SMe2 / tetrahydrofuran / 6 h / 0 - 20 °C View Scheme

1: 1.60 g / Br2 / acetic acid / 12 h / 80 °C 2: 85 percent / (tol)3P; triethylamine / Pd(OAc)2 / acetonitrile / 16 h / 120 °C 3: 87 percent / H2 / Pd/C / ethanol 4: 74 percent / AlCl3; LiAlH4 / tetrahydrofuran / 20 h / Heating View Scheme

1: 87 percent / H2 / Pd/C / ethanol 2: 74 percent / AlCl3; LiAlH4 / tetrahydrofuran / 20 h / Heating View Scheme

1: 100 percent / H2 / Pd/C / methanol / 760 Torr 2: 78 percent / aq. HBr / Heating 3: 86 percent / NaOMe / methanol / Heating View Scheme

1: 80 percent / PdCl2(PPh3)2; Et3N / tetrahydrofuran / Heating 2: 100 percent / H2 / Pd/C / methanol / 760 Torr 3: 78 percent / aq. HBr / Heating 4: 86 percent / NaOMe / methanol / Heating View Scheme

1: 81 percent / dimethylformamide / 8 h / 140 °C 2: 90 percent / BH3*SMe2 / tetrahydrofuran / 2 h / 0 °C 3: 80 percent / BH3*SMe2 / tetrahydrofuran / 6 h / 0 - 20 °C View Scheme