tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; benzene T=20°C; Suzuki coupling; 3 h;

1.1: PPh3 / Pd(OAc)2 / tetrahydrofuran / 0.25 h / Heating 1.2: 70.4 mg / TBAF / tetrahydrofuran / 0.5 h / Heating View Scheme

1.1: K2CO3 / H2O; acetone / 4 h / Heating 2.1: PPh3 / Pd(OAc)2 / tetrahydrofuran / 0.25 h / Heating 2.2: 70.4 mg / TBAF / tetrahydrofuran / 0.5 h / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; benzene 18 h; Heating;

1: 5-bromo-2-methoxy-cyclohepta-2,4,6-trien-1-one With triphenylphosphine; palladium diacetate in tetrahydrofuran 0.25 h; Heating; 2: 4-(triethoxysilyl)-1,2,3-trimethoxybenzene With tetrabutyl ammonium fluoride in tetrahydrofuran Hiyama cross-coupling reaction; 0.5 h; Heating;

1.1: sodium nitrite / H2O / 0.5 h / 20 °C 1.2: 92 percent / acetic acid / H2O / 0.5 h 2.1: 97 percent / hydrogen / Pd/carbon / methanol / 2 h / 749.87 Torr 3.1: hydrochloric acid; sodium nitrite / H2O / 0.25 h / -20 °C 3.2: 79 percent / potassium iodide / H2O / 0.75 h / 50 - 55 °C 4.1: 70 percent / CH2Cl2 5.1: 93 percent / tetrakis(triphenylphosphine)palladium(0); Na2CO3 / benzene; ethanol / 3 h / 20 °C View Scheme

tetrabutyl ammonium fluoride; palladium diacetate; triphenylphosphine in tetrahydrofuran

1.1: hydrochloric acid; sodium nitrite / H2O / 0.25 h / -20 °C 1.2: 79 percent / potassium iodide / H2O / 0.75 h / 50 - 55 °C 2.1: 70 percent / CH2Cl2 3.1: 93 percent / tetrakis(triphenylphosphine)palladium(0); Na2CO3 / benzene; ethanol / 3 h / 20 °C View Scheme

1: 70 percent / CH2Cl2 2: 93 percent / tetrakis(triphenylphosphine)palladium(0); Na2CO3 / benzene; ethanol / 3 h / 20 °C View Scheme

1.1: t-butyllithium / diethyl ether / 0.5 h / -95 °C 1.2: triisopropyl borate / diethyl ether / 0.33 h / -95 °C 1.3: acidic silica gel 2.1: 93 percent / tetrakis(triphenylphosphine)palladium(0); Na2CO3 / benzene; ethanol / 3 h / 20 °C View Scheme