tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether T=20°C; 0.166667 h;

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -65 °C 1.2: trimethyl borate / tetrahydrofuran; hexane / -65 - 20 °C 1.3: 82 percent / aq.HCl / tetrahydrofuran; hexane / pH 6 - 7 2.1: 86 percent / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 0.17 h / 20 °C View Scheme

1: 70 percent / sulfuric acid / 6 h / Heating 2: 86 percent / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 0.17 h / 20 °C View Scheme

1.1: potassium carbonate; potassium iodide / acetone / 48 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 2.2: trialkyl borate / -78 - 20 °C / Inert atmosphere 2.3: Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 5 h / 80 °C / Inert atmosphere View Scheme

1.1: potassium carbonate; potassium iodide / acetone / 48 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 2.2: trialkyl borate / -78 - 20 °C / Inert atmosphere 2.3: Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 5 h / 80 °C / Inert atmosphere View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethylene glycol dimethyl ether; water 15 h; Reflux;