hydrogen; Rh/Al2O3 in ethanol T=20°C; 2 h;

1.1: 93 percent / di-isopropylethyl amine / CH2Cl2 / 2 h / 0 °C 2.1: hexamethylditin; bis(diphenylphosphinyl)ferrocene; LiCl / Pd(PPh3)4 / dioxane / 72 h / 110 °C 2.2: 75 percent / NBS / tetrahydrofuran / 1 h / 20 °C 3.1: 92 percent / H2 / Rh/Al2O3 / ethanol / 2 h / 20 °C View Scheme

1.1: t-BuLi / diethyl ether / -78 - 20 °C 1.2: TsOH / toluene / 20 - 50 °C 2.1: 92 percent / H2 / Rh/Al2O3 / ethanol / 2 h / 20 °C View Scheme

1.1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 20 °C 2.1: t-BuLi / diethyl ether / -78 - 20 °C 2.2: TsOH / toluene / 20 - 50 °C 3.1: 92 percent / H2 / Rh/Al2O3 / ethanol / 2 h / 20 °C View Scheme

1.1: 75 percent / ethanol / 24 h / 25 °C 2.1: tert-BuLi / diethyl ether; pentane / 7 h / -20 °C 2.2: (BrCl2C)2 / diethyl ether / -78 - 20 °C 3.1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 20 °C 4.1: t-BuLi / diethyl ether / -78 - 20 °C 4.2: TsOH / toluene / 20 - 50 °C 5.1: 92 percent / H2 / Rh/Al2O3 / ethanol / 2 h / 20 °C View Scheme