iodine; iodic acid in methanol; water 48 h; Heating;

1: Et3N / CH2Cl2 / 1 h / 0 °C 2: 2.1 g / ICl / CH2Cl2 / 20 °C View Scheme

1: 84 percent / CuI; PPh3; iPr2NH / Pd(PPh3)2Cl2 / 16 h / 25 °C 2: 90 percent / KOH / methanol; H2O / 20 h / 25 °C 3: 98 percent / Cp2TiMe2 / toluene / 16 h / 110 °C 4: HCOOH; NEt3 / Noyori's catalyst / dimethylformamide / 7 h / 25 °C View Scheme

1: 84 percent / CuI; PPh3; iPr2NH / Pd(PPh3)2Cl2 / 16 h / 25 °C 2: 90 percent / KOH / methanol; H2O / 20 h / 25 °C 3: 98 percent / Cp2TiMe2 / toluene / 16 h / 110 °C 4: HCOOH; NEt3 / Noyori's catalyst / dimethylformamide / 7 h / 25 °C View Scheme

1: 84 percent / CuI; PPh3; iPr2NH / Pd(PPh3)2Cl2 / 16 h / 25 °C 2: 90 percent / KOH / methanol; H2O / 20 h / 25 °C 3: 98 percent / Cp2TiMe2 / toluene / 16 h / 110 °C View Scheme

1.1: 84 percent / CuI; PPh3; iPr2NH / Pd(PPh3)2Cl2 / 16 h / 25 °C 2.1: 90 percent / KOH / methanol; H2O / 20 h / 25 °C 3.1: 98 percent / Cp2TiMe2 / toluene / 16 h / 110 °C 4.1: HCOOH; NEt3 / Noyori's catalist / dimethylformamide / 7 h / 25 °C 4.2: methanol; H2O / 3 h / 25 °C 4.3: NaBH4 / methanol; H2O / 16 h / 25 °C View Scheme

1.1: potassium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 - 5 °C / Inert atmosphere 1.2: 17 h / 20 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / methanol; water / 2 h / 20 °C 3.1: copper diacetate; palladium diacetate; potassium carbonate / toluene / 24 h / Inert atmosphere; Reflux View Scheme

1.1: potassium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 - 5 °C / Inert atmosphere 1.2: 17 h / 20 °C / Inert atmosphere; Reflux 2.1: potassium carbonate / methanol; water / 2 h / 20 °C 3.1: copper diacetate; palladium diacetate; potassium carbonate / toluene / 24 h / Inert atmosphere; Reflux View Scheme