palladium diacetate; caesium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in 1,4-dioxane T=100°C; 24 h;

1: isopropyl alcohol With sodium hydride T=20°C; 0.5 h; Inert atmosphere; 2: 4-bromo-2-chloro-pyridine T=150°C; 0.5 h; Microwave irradiation;

1.1: lithium diisopropylamide / tetrahydrofuran / -70 °C 1.2: 82 percent / iodine / tetrahydrofuran / -70 °C 2.1: 80 percent / sodium acetate; potassium bromide / palladium(II) acetate / various solvent(s) / 90 - 100 °C 3.1: 91 percent / tetrabutylammonium bromide; triphenylphosphine; sodium carbonate / palladium(II) acetate; potassium chloride / toluene; H2O / Heating 4.1: 88 percent / 3-chloroperoxybenzoic acid / toluene / 24 h / 20 °C 5.1: 85 percent / phosphorus oxychloride View Scheme

1: zinc; lithium chloride / 2 h / 20 °C / |Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: lithium diisopropylamide / tetrahydrofuran / -70 °C 1.2: 82 percent / iodine / tetrahydrofuran / -70 °C 2.1: 80 percent / sodium acetate; potassium bromide / palladium(II) acetate / various solvent(s) / 90 - 100 °C View Scheme

1: benzyl alcohol With sodium hydride in tetrahydrofuran; mineral oil T=0°C; 4 h; 2: 4-bromo-2-chloro-pyridine in tetrahydrofuran; mineral oil T=0 - 25°C;

sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in toluene T=85°C; 20 h; Inert atmosphere;

1: zinc; lithium chloride / 2 h / 20 °C / |Inert atmosphere 2: lithium chloride; copper(l) iodide / tetrahydrofuran / 24 h / 20 °C View Scheme