tetrakis(triphenylphosphine) palladium(0); triethylamine in acetonitrile T=70°C; 2 h;

1: pyridine / 8 h / 0 °C 2: DIBAL-H / toluene / 7 h / -78 °C 3: dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C 4: NaI / dimethylsulfoxide / 5 h / Ambient temperature 5: 100 percent / 5 mole percent Pd(PPh3)4, N(C2H5)3 / acetonitrile / 2 h / 70 °C View Scheme

1: dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C 2: NaI / dimethylsulfoxide / 5 h / Ambient temperature 3: 100 percent / 5 mole percent Pd(PPh3)4, N(C2H5)3 / acetonitrile / 2 h / 70 °C View Scheme

1: DIBAL-H / toluene / 7 h / -78 °C 2: dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C 3: NaI / dimethylsulfoxide / 5 h / Ambient temperature 4: 100 percent / 5 mole percent Pd(PPh3)4, N(C2H5)3 / acetonitrile / 2 h / 70 °C View Scheme

1: NaI / dimethylsulfoxide / 5 h / Ambient temperature 2: 100 percent / 5 mole percent Pd(PPh3)4, N(C2H5)3 / acetonitrile / 2 h / 70 °C View Scheme

1.1: trifluoromethylsulfonic anhydride; 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.75 h / -78 °C / |Inert atmosphere 1.2: 1 h / -78 - 20 °C / |Inert atmosphere 1.3: 3 h / 20 °C / |Inert atmosphere 2.1: acetyl chloride / methanol / 0.5 h / 20 °C / |Inert atmosphere 2.2: 2 h / |Reflux; |Inert atmosphere View Scheme