tetrakis(triphenylphosphine) palladium(0); cesium fluoride in ethylene glycol dimethyl ether Suzuki-Miyaura cross coupling reaction; 3 h; RefluxInert atmosphere;

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 1.2: trimethylborate / tetrahydrofuran / 0.5 h / -78 °C 1.3: HCl / tetrahydrofuran; H2O 2.1: 87 percent / sodium carbonate / Pd(PPh3)4 / ethanol; H2O; 1,2-dimethoxy-ethane / 46 h / Heating View Scheme

1: 69 percent / selenium / dimethylsulfoxide / 0.08 h / 170 °C 2: 87 percent / sodium carbonate / Pd(PPh3)4 / ethanol; H2O; 1,2-dimethoxy-ethane / 46 h / Heating View Scheme

1.1: phosphorus tribromide / CH2Cl2 / 1 h / 0 °C 1.2: 70 percent / CH2Cl2 / 1 h / Heating 2.1: 69 percent / selenium / dimethylsulfoxide / 0.08 h / 170 °C 3.1: 87 percent / sodium carbonate / Pd(PPh3)4 / ethanol; H2O; 1,2-dimethoxy-ethane / 46 h / Heating View Scheme