sodium carbonate; potassium iodide in toluene Heating;

1: 85 percent / diethyl ether; tetrahydrofuran / 5 h / Heating 2: 93 percent / H2 / HRh(CO)(PPh3)3 / toluene / 5 h / 60 °C / 76000 Torr 3: 90 percent / NaBH4; aq. NaOH / methanol / 3 h / 20 °C 4: 85 percent / H2 / 10 percent Pd/C / aq. ethanol / Heating 5: 80 percent / Br2; PPh3 / acetonitrile / 2 h / 20 °C 6: 75 percent / Na2CO3; KI / toluene / Heating View Scheme

1: 61 percent / PPh3; H2 / HRh(CO)(PPh3)3 / toluene / 24 h / 100 °C / 76000 Torr 2: 90 percent / NaBH4; aq. NaOH / methanol / 3 h / 20 °C 3: 85 percent / H2 / 10 percent Pd/C / aq. ethanol / Heating 4: 80 percent / Br2; PPh3 / acetonitrile / 2 h / 20 °C 5: 75 percent / Na2CO3; KI / toluene / Heating View Scheme

1: 93 percent / H2 / HRh(CO)(PPh3)3 / toluene / 5 h / 60 °C / 76000 Torr 2: 90 percent / NaBH4; aq. NaOH / methanol / 3 h / 20 °C 3: 85 percent / H2 / 10 percent Pd/C / aq. ethanol / Heating 4: 80 percent / Br2; PPh3 / acetonitrile / 2 h / 20 °C 5: 75 percent / Na2CO3; KI / toluene / Heating View Scheme

1: 90 percent / NaBH4; aq. NaOH / methanol / 3 h / 20 °C 2: 85 percent / H2 / 10 percent Pd/C / aq. ethanol / Heating 3: 80 percent / Br2; PPh3 / acetonitrile / 2 h / 20 °C 4: 75 percent / Na2CO3; KI / toluene / Heating View Scheme

1: 85 percent / H2 / 10 percent Pd/C / aq. ethanol / Heating 2: 80 percent / Br2; PPh3 / acetonitrile / 2 h / 20 °C 3: 75 percent / Na2CO3; KI / toluene / Heating View Scheme

1: 80 percent / Br2; PPh3 / acetonitrile / 2 h / 20 °C 2: 75 percent / Na2CO3; KI / toluene / Heating View Scheme