caesium carbonate; copper(l) chloride in acetonitrile T=20°C; 35 h; Inert atmosphere;

1: 79 percent / tin, hydrochloric acid / methanol / 80 °C 2: 1.) K2CO3; 2.) manganese dioxide / 1.) THF, 65 deg C, 12 h; 2.) CH2Cl2, 40 deg C, 24 h View Scheme

1: 93 percent / o-xylene / 14 h / 140 °C 2: 79 percent / tin, hydrochloric acid / methanol / 80 °C 3: 1.) K2CO3; 2.) manganese dioxide / 1.) THF, 65 deg C, 12 h; 2.) CH2Cl2, 40 deg C, 24 h View Scheme

1: 87 percent / 1.) NaNO2; 2.) H2SO4 / H2O / Heating 2: 81 percent / KI, K2CO3 / acetonitrile / 48 h / 82 °C 3: 93 percent / o-xylene / 14 h / 140 °C 4: 79 percent / tin, hydrochloric acid / methanol / 80 °C 5: 1.) K2CO3; 2.) manganese dioxide / 1.) THF, 65 deg C, 12 h; 2.) CH2Cl2, 40 deg C, 24 h View Scheme

1.1: iron; acetic acid / 4 h / 45 °C / |Inert atmosphere 2.1: caesium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 16 h / |Inert atmosphere; |Reflux 3.1: potassium carbonate; palladium diacetate; 2-oxo-3,3-dimethyl-butanoic acid / 23 h / 85 °C / |Inert atmosphere 4.1: palladium 10 on activated carbon; hydrogen / methanol; dichloromethane / 72 h / 20 °C / |Inert atmosphere 5.1: caesium carbonate; copper(l) iodide / acetonitrile / 29 h / 20 °C / |Inert atmosphere 5.2: 29 h / 111 °C / |Inert atmosphere View Scheme

1.1: iron; acetic acid / 3.5 h / 45 °C / |Inert atmosphere 2.1: caesium carbonate; palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine / toluene / 26 h / 100 °C / |Inert atmosphere 3.1: potassium carbonate; palladium diacetate; 2-oxo-3,3-dimethyl-butanoic acid / toluene / 31.5 h / 100 °C / |Inert atmosphere 4.1: boron tribromide / dichloromethane / 15.5 h / -78 - 20 °C / |Inert atmosphere 5.1: caesium carbonate; copper(l) iodide / acetonitrile / 29 h / 20 °C / |Inert atmosphere 5.2: 29 h / 111 °C / |Inert atmosphere View Scheme

1: 75 percent / pyridine / 0 - 5 °C 2: 40 percent / AlCl3 / nitrobenzene / 0 - 5 °C 3: methanol 4: NaBH4 / methanol 5: pyridine / benzene 6: various solvent(s) / 6 h / Heating 7: 25 percent / LiAlH4 / tetrahydrofuran / 1.) 3 h, room temp., 2.) 8 h, reflux View Scheme

1: 75 percent / pyridine / 0 - 5 °C 2: 40 percent / AlCl3 / nitrobenzene / 0 - 5 °C 3: methanol 4: NaBH4 / methanol 5: pyridine / benzene 6: various solvent(s) / 6 h / Heating 7: 25 percent / LiAlH4 / tetrahydrofuran / 1.) 3 h, room temp., 2.) 8 h, reflux View Scheme

1: 40 percent / AlCl3 / nitrobenzene / 0 - 5 °C 2: methanol 3: NaBH4 / methanol 4: pyridine / benzene 5: various solvent(s) / 6 h / Heating 6: 25 percent / LiAlH4 / tetrahydrofuran / 1.) 3 h, room temp., 2.) 8 h, reflux View Scheme

1: NaBH4 / methanol 2: pyridine / benzene 3: various solvent(s) / 6 h / Heating 4: 25 percent / LiAlH4 / tetrahydrofuran / 1.) 3 h, room temp., 2.) 8 h, reflux View Scheme