copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; 24 h;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine in tetrahydrofuran T=20°C; Sonogashira coupling; 24 h;

1.1: 62 percent / NaOH / dimethylformamide / 48 h / Heating 2.1: 97 percent / HNO3 / CHCl3; acetic acid / 18 h / 20 °C 3.1: 92 percent / aq. HCl; tin / tetrahydrofuran / 18 h / 20 °C 4.1: BF3*Et2O; tBuNO2 / tetrahydrofuran / 3 h / -8 °C 4.2: 95 percent / K2CO3; H2O; acetonitrile / tetrahydrofuran / 0.25 h / -15 °C 5.1: 62 percent / Cu(OAc)2 / PdCl2; PPh3 / triethylamine / 18 h / 100 °C 6.1: 88 percent / MeI / 18 h / 120 °C View Scheme

1.1: 92 percent / aq. HCl; tin / tetrahydrofuran / 18 h / 20 °C 2.1: BF3*Et2O; tBuNO2 / tetrahydrofuran / 3 h / -8 °C 2.2: 95 percent / K2CO3; H2O; acetonitrile / tetrahydrofuran / 0.25 h / -15 °C 3.1: 62 percent / Cu(OAc)2 / PdCl2; PPh3 / triethylamine / 18 h / 100 °C 4.1: 88 percent / MeI / 18 h / 120 °C View Scheme

1.1: BF3*Et2O; tBuNO2 / tetrahydrofuran / 3 h / -8 °C 1.2: 95 percent / K2CO3; H2O; acetonitrile / tetrahydrofuran / 0.25 h / -15 °C 2.1: 62 percent / Cu(OAc)2 / PdCl2; PPh3 / triethylamine / 18 h / 100 °C 3.1: 88 percent / MeI / 18 h / 120 °C View Scheme

1.1: 62 percent / NaOH / dimethylformamide / 48 h / Heating 2.1: 97 percent / HNO3 / CHCl3; acetic acid / 18 h / 20 °C 3.1: 92 percent / aq. HCl; tin / tetrahydrofuran / 18 h / 20 °C 4.1: BF3*Et2O; tBuNO2 / tetrahydrofuran / 3 h / -8 °C 4.2: 95 percent / K2CO3; H2O; acetonitrile / tetrahydrofuran / 0.25 h / -15 °C 5.1: 62 percent / Cu(OAc)2 / PdCl2; PPh3 / triethylamine / 18 h / 100 °C 6.1: 88 percent / MeI / 18 h / 120 °C View Scheme

1.1: 97 percent / HNO3 / CHCl3; acetic acid / 18 h / 20 °C 2.1: 92 percent / aq. HCl; tin / tetrahydrofuran / 18 h / 20 °C 3.1: BF3*Et2O; tBuNO2 / tetrahydrofuran / 3 h / -8 °C 3.2: 95 percent / K2CO3; H2O; acetonitrile / tetrahydrofuran / 0.25 h / -15 °C 4.1: 62 percent / Cu(OAc)2 / PdCl2; PPh3 / triethylamine / 18 h / 100 °C 5.1: 88 percent / MeI / 18 h / 120 °C View Scheme

1: mercury(II) diacetate; iodine / dichloromethane / 12 h / 20 °C 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 12 h / 60 °C 2.1: mercury(II) diacetate; iodine / dichloromethane / 12 h / 20 °C 3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere View Scheme