1: With triphenylphosphine in tetrahydrofuran T=20°C; 15 h; 2: With water in tetrahydrofuran T=20°C; 3 h;

1.1: aq. NaOH / 6 h / 100 °C 2.1: NaN3 / dimethylformamide / 2.5 h / 110 °C 3.1: PPh3 / tetrahydrofuran / 15 h / 20 °C 3.2: 86 percent / H2O / tetrahydrofuran / 3 h / 20 °C View Scheme

1.1: NaN3 / dimethylformamide / 2.5 h / 110 °C 2.1: PPh3 / tetrahydrofuran / 15 h / 20 °C 2.2: 86 percent / H2O / tetrahydrofuran / 3 h / 20 °C View Scheme

sodium hydride; tert-butyl alcohol; IPr*hydrochloride; palladium diacetate in 1,4-dioxane 8 h;