triphenylphosphine in tetrahydrofuran; water

1.1: cesium fluoride; tetrabutyl-ammonium chloride; bis-triphenylphosphine-palladium(II) chloride / toluene; water / 18 h / 20 °C / |Inert atmosphere 2.1: acetic acid / chloroform / 1 h / 0 - 20 °C 2.2: 20 °C 3.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2 h / 80 °C 4.1: nickel dichloride; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C View Scheme

1: 72 percent / Pd(OAc)2, PPh3, Ag2CO3 / dimethylformamide / 24 h / 60 °C 2: 1N HCl / tetrahydrofuran / 24 h / Ambient temperature 3: 58 percent / Ag2CO3 / toluene / 8 h / 90 °C 4: 3 N KOH / tetrahydrofuran 6: 73 percent / DPPA, EtO2CN=NCO2Et, PPh3 / tetrahydrofuran 7: 81 percent / PPh3 / tetrahydrofuran; H2O View Scheme

1: 3 N KOH / tetrahydrofuran 3: 73 percent / DPPA, EtO2CN=NCO2Et, PPh3 / tetrahydrofuran 4: 81 percent / PPh3 / tetrahydrofuran; H2O View Scheme

1: 58 percent / Ag2CO3 / toluene / 8 h / 90 °C 2: 3 N KOH / tetrahydrofuran 4: 73 percent / DPPA, EtO2CN=NCO2Et, PPh3 / tetrahydrofuran 5: 81 percent / PPh3 / tetrahydrofuran; H2O View Scheme

1: 73 percent / DPPA, EtO2CN=NCO2Et, PPh3 / tetrahydrofuran 2: 81 percent / PPh3 / tetrahydrofuran; H2O View Scheme

hydrogenchloride; water in water 16 h; Reflux;