tetrakis(triphenylphosphine) palladium(0); sodium hydroxide in ethylene glycol dimethyl ether; water T=85°C; Suzuki coupling; 40 h; Inert atmosphere;

1: sodium hydrogencarbonate / ethanol / 12 h / 20 °C 2: pyridine; iodine / 5 h / 50 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / ethylene glycol dimethyl ether; water / 40 h / 85 °C / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -78 - 20 °C 1.2: 16 h / 20 °C 1.3: pH 1 2.1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / ethylene glycol dimethyl ether; water / 40 h / 85 °C / Inert atmosphere View Scheme

1: N-bromosuccinmide; ammonium acetate / diethyl ether / 0.5 h / 25 °C 2: sodium hydrogencarbonate / ethanol / 12 h / 20 °C 3: pyridine; iodine / 5 h / 50 °C 4: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / ethylene glycol dimethyl ether; water / 40 h / 85 °C / Inert atmosphere View Scheme

1: sodium hydrogencarbonate / ethanol / 12 h / 20 °C 2: pyridine; iodine / 5 h / 50 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / ethylene glycol dimethyl ether; water / 40 h / 85 °C / Inert atmosphere View Scheme