borane-THF in tetrahydrofuran T=20°C; 3 h;

1: 94 percent / NaI; K2CO3 / dimethylformamide / 40 - 60 °C 2: 94 percent / p-toluenesulfonic acid / toluene / 5 h / Heating 3: 98 percent / Pd(OAc)2; [Bu4N]Br; KOAc / dimethylformamide / 3 h / Heating 4: 96 percent / aq. HCl / tetrahydrofuran / 5 h / Heating 5: 92 percent / BH3*THF / tetrahydrofuran / 3 h / 20 °C View Scheme

1: 94 percent / NaI; K2CO3 / dimethylformamide / 40 - 60 °C 2: 94 percent / p-toluenesulfonic acid / toluene / 5 h / Heating 3: 98 percent / Pd(OAc)2; [Bu4N]Br; KOAc / dimethylformamide / 3 h / Heating 4: 96 percent / aq. HCl / tetrahydrofuran / 5 h / Heating 5: 92 percent / BH3*THF / tetrahydrofuran / 3 h / 20 °C View Scheme

1: 94 percent / p-toluenesulfonic acid / toluene / 5 h / Heating 2: 98 percent / Pd(OAc)2; [Bu4N]Br; KOAc / dimethylformamide / 3 h / Heating 3: 96 percent / aq. HCl / tetrahydrofuran / 5 h / Heating 4: 92 percent / BH3*THF / tetrahydrofuran / 3 h / 20 °C View Scheme

1: 96 percent / aq. HCl / tetrahydrofuran / 5 h / Heating 2: 92 percent / BH3*THF / tetrahydrofuran / 3 h / 20 °C View Scheme

1: 98 percent / Pd(OAc)2; [Bu4N]Br; KOAc / dimethylformamide / 3 h / Heating 2: 96 percent / aq. HCl / tetrahydrofuran / 5 h / Heating 3: 92 percent / BH3*THF / tetrahydrofuran / 3 h / 20 °C View Scheme