hydrogen fluoride; NAF in tetrahydrofuran T=25°C; 24 h;

1: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature 2: 62 percent / TBAF / tetrahydrofuran / 0 °C View Scheme

1: imidazole / dimethylformamide / Ambient temperature 2: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature 3: 92 percent / formic acid / 0 °C 4: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature 5: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature 6: 62 percent / TBAF / tetrahydrofuran / 0 °C View Scheme

1: 92 percent / formic acid / 0 °C 2: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature 3: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature 4: 62 percent / TBAF / tetrahydrofuran / 0 °C View Scheme

1: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature 2: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature 3: 62 percent / TBAF / tetrahydrofuran / 0 °C View Scheme

1: 83 percent / NaBH4, nickel(II) chloride*6 H2O / methanol / Ambient temperature 2: 92 percent / formic acid / 0 °C 3: 95 percent / borane-THF / tetrahydrofuran / Ambient temperature 4: 78 percent / nitrosonium tetrafluoroborate, Et3N / diethyl ether / Ambient temperature 5: 62 percent / TBAF / tetrahydrofuran / 0 °C View Scheme

1: imidazole / dimethylformamide / 24 h / -23 - 25 °C 2: 81 percent / NaNO2, aq. HCl / tetrahydrofuran / 3 h / 0 °C 3: 66 percent / HF, NaF / tetrahydrofuran / 24 h / 25 °C View Scheme

1: 83 percent / TEA / dioxane; H2O / 24 h / 25 °C 2: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 1 h, 2.) DMF, from -23 deg C to 0 deg C, 3 h 3: BBr3 / CH2Cl2 / 7 h / Ambient temperature 4: imidazole / dimethylformamide / 24 h / -23 - 25 °C 5: 81 percent / NaNO2, aq. HCl / tetrahydrofuran / 3 h / 0 °C 6: 66 percent / HF, NaF / tetrahydrofuran / 24 h / 25 °C View Scheme