1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in N,N-dimethyl-formamide T=20°C; 1 h;

2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane 24 h; Heating;

1: 86 percent / BBr3 / CH2Cl2 / -20 - 20 °C 2: 92.2 percent / o-iodoxybenzoic acid / dimethylformamide / 1 h / 20 °C View Scheme

1: 95 percent / t-BuOK / diethyl ether; tetrahydrofuran / 20 °C 2: 88 percent / MeSO3H / CH2Cl2 / 0 °C 3: 86 percent / BBr3 / CH2Cl2 / -20 - 20 °C 4: 92.2 percent / o-iodoxybenzoic acid / dimethylformamide / 1 h / 20 °C View Scheme

1: 60 percent / I2; 1,2-epoxybutane / benzene / 1 h / Irradiation 2: 86 percent / BBr3 / CH2Cl2 / -20 - 20 °C 3: 92.2 percent / o-iodoxybenzoic acid / dimethylformamide / 1 h / 20 °C View Scheme

1: 88 percent / MeSO3H / CH2Cl2 / 0 °C 2: 86 percent / BBr3 / CH2Cl2 / -20 - 20 °C 3: 92.2 percent / o-iodoxybenzoic acid / dimethylformamide / 1 h / 20 °C View Scheme

1: potassium phosphate; biphenyl-4-yl(di-tert-butylphosphine); palladium diacetate / tetrahydrofuran / 40 °C 2: 10 palladium on activated charcoal; hydrogen 3: pyridine 4: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / N,N-dimethyl-formamide 5: methanol; potassium carbonate / tetrahydrofuran 6: platinum (II) chloride 7: boron tribromide 8: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione View Scheme

1: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / 1,4-dioxane / Reflux 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine 3: methanol; potassium carbonate / tetrahydrofuran 4: platinum (II) chloride 5: boron tribromide 6: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione View Scheme

1: boron tribromide 2: Basic conditions 3: potassium phosphate; biphenyl-4-yl(di-tert-butylphosphine); palladium diacetate / tetrahydrofuran / 40 °C 4: 10 palladium on activated charcoal; hydrogen 5: pyridine 6: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / N,N-dimethyl-formamide 7: methanol; potassium carbonate / tetrahydrofuran 8: platinum (II) chloride 9: boron tribromide 10: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione View Scheme

1: Basic conditions 2: potassium phosphate; biphenyl-4-yl(di-tert-butylphosphine); palladium diacetate / tetrahydrofuran / 40 °C 3: 10 palladium on activated charcoal; hydrogen 4: pyridine 5: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / N,N-dimethyl-formamide 6: methanol; potassium carbonate / tetrahydrofuran 7: platinum (II) chloride 8: boron tribromide 9: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione View Scheme