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 View Scheme

potassium carbonate in N,N-dimethyl-formamide T=20°C; 3 h;

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

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 10: sodium tetrahydroborate / N,N-dimethyl-formamide View Scheme

aluminium trichloride in dichloromethane