potassium phosphate; 1,3-bis(2,4,6-trimethylphenyl)imidazolinium chloride; palladium diacetate in N,N-dimethyl-formamide T=50 - 80°C; Suzuki-Miyaura reaction; 13.5 h;

1: t-BuOK / 1-methyl-pyrrolidin-2-one; tetrahydrofuran / 3 h / 100 °C 2: POCl3; Me4NCl / 21 h / 140 °C 3: Cs2CO3 / Pd(dppf)Cl2 / toluene / 1 h / 110 °C View Scheme

1: POCl3; Me4NCl / 21 h / 140 °C 2: Cs2CO3 / Pd(dppf)Cl2 / toluene / 1 h / 110 °C View Scheme

1.1: t-BuONa; NaH / tetrahydrofuran / 20 - 25 °C 1.2: tetrahydrofuran / 23 °C 2.1: p-toluenesulfonic acid monohydrate / toluene / 20 h / 117 °C 3.1: t-BuOK / 1-methyl-pyrrolidin-2-one; tetrahydrofuran / 3 h / 100 °C 4.1: POCl3; Me4NCl / 21 h / 140 °C 5.1: Cs2CO3 / Pd(dppf)Cl2 / toluene / 1 h / 110 °C View Scheme

trichlorophosphate

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

1: 91 percent / tetrabutylammonium bromide; triphenylphosphine; sodium carbonate / palladium(II) acetate; potassium chloride / toluene; H2O / Heating 2: 88 percent / 3-chloroperoxybenzoic acid / toluene / 24 h / 20 °C 3: 85 percent / phosphorus oxychloride 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 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

1.1: 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 3.1: 80 percent / sodium acetate; potassium bromide / palladium(II) acetate / various solvent(s) / 90 - 100 °C 4.1: 91 percent / tetrabutylammonium bromide; triphenylphosphine; sodium carbonate / palladium(II) acetate; potassium chloride / toluene; H2O / Heating 5.1: 88 percent / 3-chloroperoxybenzoic acid / toluene / 24 h / 20 °C 6.1: 85 percent / phosphorus oxychloride 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