1: 4-iodo-benzoic acid methyl ester With lithium chloride in N,N-dimethyl-formamide T=80°C; 2: methyl 2-iodobenzoate With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in N,N-dimethyl-formamide T=80°C; 2 h; Inert atmosphere;

bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tri-cyclo-hexyl-phosphine in tetrahydrofuran T=25°C; 12 h; Inert atmosphere;

potassium phosphate; trans-[Ni(Naph)Cl(PPh3)2]; tri-cyclo-hexyl-phosphine in tetrahydrofuran T=25°C; Suzuki coupling; 12 h; Inert atmosphere;

potassium phosphate; trans-[Ni(Naph)Cl(PPh3)2]; tri-cyclo-hexyl-phosphine in tetrahydrofuran T=25°C; Suzuki coupling; 14 h; Inert atmosphere;

potassium phosphate; trans-[Ni(Naph)Cl(PPh3)2]; tri-cyclo-hexyl-phosphine in tetrahydrofuran T=25°C; Suzuki coupling; 12 h; Inert atmosphere;

1.1: sodium hydride / ethylene glycol dimethyl ether / 0.17 h / 0 - 20 °C / Inert atmosphere 1.2: 12 h / 0 - 20 °C / Inert atmosphere 2.1: potassium phosphate; bis(1,5-cyclooctadiene)nickel (0); tri-cyclo-hexyl-phosphine / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere View Scheme

oxygen; palladium diacetate T=100°C; oxidative coupling; P=38000 Torr; Product distribution; Further Variations:CatalystsTemperatures;

sodium carbonate