potassium fluoride; palladium diacetate; 2-dicyclohexylphosphino-1,1'-biphenyl in tetrahydrofuran T=60°C; 18 h;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water T=95°C; Suzuki reaction;

1.1: 100 percent / imidazole / dimethylformamide / 20 °C 2.1: n-butyl lithium / tetrahydrofuran / 0.5 h / -78 °C 2.2: triisopropyl borate / tetrahydrofuran / -78 - 20 °C 2.3: 65 percent / HCl / tetrahydrofuran; H2O / 0.08 h / 0 °C 3.1: 62 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 95 °C View Scheme

1.1: n-butyl lithium / tetrahydrofuran / 0.5 h / -78 °C 1.2: triisopropyl borate / tetrahydrofuran / -78 - 20 °C 1.3: 65 percent / HCl / tetrahydrofuran; H2O / 0.08 h / 0 °C 2.1: 62 percent / Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 95 °C View Scheme