1: With lithium diisopropyl amide in tetrahydrofuran T=-70°C; 2: With iodine in tetrahydrofuran T=-70°C;

1.1: hydrobromic acid; sodium nitrite / H2O 1.2: 97 percent / potassium bromide / H2O 2.1: lithium diisopropylamide / tetrahydrofuran / -70 °C 2.2: 82 percent / iodine / tetrahydrofuran / -70 °C View Scheme

1: 80 percent / sodium acetate; potassium bromide / palladium(II) acetate / various solvent(s) / 90 - 100 °C 2: 91 percent / tetrabutylammonium bromide; triphenylphosphine; sodium carbonate / palladium(II) acetate; potassium chloride / toluene; H2O / Heating 3: 88 percent / 3-chloroperoxybenzoic acid / toluene / 24 h / 20 °C 4: 85 percent / phosphorus oxychloride View Scheme

sodium acetate; potassium bromide; palladium diacetate in various solvent(s) T=90 - 100°C; Heck coupling;

sodium acetate; potassium bromide; palladium diacetate in water T=90°C; Heck reaction;