n-butyllithium; copper(I) bromide dimethylsulfide complex in tetrahydrofuran; hexane T=-78 - -10°C; 2 h;

palladium diacetate; triethylamine; triphenylphosphine in water; acetonitrile T=20°C; 2 h;

palladium diacetate; triethylamine; triphenylphosphine in water; acetonitrile 2 h; RefluxInert atmosphere;

1: [Ir(COD)(PPh3)2]OTf-H2 / CH2Cl2 / 16 h / 70 °C 2: HCl / methanol View Scheme

palladium diacetate; triphenylphosphine in acetonitrile 2 h; RefluxInert atmosphere;

1: 90 percent / aq. 12 M HCl / 1 h / Heating 2: 91 percent / aq. 12 M HCl / 12 h / 25 °C 3: 1.) n-BuLi / 1.) DME, hexane, -78 deg C, 30 min, 2.) -78 deg C, 30 min, up to room temp. within 3h 4: p-TsOH / H2O; tetrahydrofuran / 3 h / Heating 5: 85 percent / aq. 8 N H2CrO4 / acetone / 0.17 h / 0 - 5 °C 6: 73 percent / NaOH / H2O; tetrahydrofuran / 2.5 h / Heating; var. of temp. View Scheme

1: 91 percent / aq. 12 M HCl / 12 h / 25 °C 2: 1.) n-BuLi / 1.) DME, hexane, -78 deg C, 30 min, 2.) -78 deg C, 30 min, up to room temp. within 3h 3: p-TsOH / H2O; tetrahydrofuran / 3 h / Heating 4: 85 percent / aq. 8 N H2CrO4 / acetone / 0.17 h / 0 - 5 °C 5: 73 percent / NaOH / H2O; tetrahydrofuran / 2.5 h / Heating; var. of temp. View Scheme

1: 1.) n-BuLi / 1.) DME, hexane, -78 deg C, 30 min, 2.) -78 deg C, 30 min, up to room temp. within 3h 2: p-TsOH / H2O; tetrahydrofuran / 3 h / Heating 3: 85 percent / aq. 8 N H2CrO4 / acetone / 0.17 h / 0 - 5 °C 4: 73 percent / NaOH / H2O; tetrahydrofuran / 2.5 h / Heating; var. of temp. View Scheme

1: 85 percent / aq. 8 N H2CrO4 / acetone / 0.17 h / 0 - 5 °C 2: 73 percent / NaOH / H2O; tetrahydrofuran / 2.5 h / Heating; var. of temp. View Scheme

1: p-TsOH / H2O; tetrahydrofuran / 3 h / Heating 2: 85 percent / aq. 8 N H2CrO4 / acetone / 0.17 h / 0 - 5 °C 3: 73 percent / NaOH / H2O; tetrahydrofuran / 2.5 h / Heating; var. of temp. View Scheme