1: aqueous NaOH 2: CrO2Cl2 View Scheme

1.1: 1H-imidazole / N,N-dimethyl-formamide / 17.5 h / 20 °C / |Inert atmosphere 2.1: acetic acid; iron / 3 h / 60 °C / |Inert atmosphere 3.1: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate; palladium diacetate / toluene / 31 h / 100 °C / |Inert atmosphere 4.1: copper diacetate; 2,2,2-trimethylacetic acid; palladium diacetate / 3 h / 110 °C / |Microwave irradiation; |Inert atmosphere 5.1: boron tribromide / dichloromethane / 14.8 h / -78 - 20 °C / |Inert atmosphere 6.1: copper dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 29 h / 20 °C / |Inert atmosphere 6.2: 23 h / |Reflux; |Inert atmosphere 7.1: tetrabutyl ammonium fluoride / N,N-dimethyl-formamide; tetrahydrofuran / 0.17 h / -10 °C / |Inert atmosphere View Scheme

potassium carbonate in N,N-dimethyl-formamide 18 h;

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

1: potassium carbonate / acetone / 2 h / |Inert atmosphere; |Reflux 2: iron; acetic acid / 4 h / 45 °C / |Inert atmosphere 3: caesium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 16 h / |Inert atmosphere; |Reflux 4: potassium carbonate; palladium diacetate; 2-oxo-3,3-dimethyl-butanoic acid / 23 h / 85 °C / |Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / methanol; dichloromethane / 72 h / 20 °C / |Inert atmosphere 6: caesium carbonate; copper(l) chloride / acetonitrile / 35 h / 20 °C / |Inert atmosphere View Scheme

1: potassium carbonate / acetone / 2 h / |Inert atmosphere; |Reflux 2: iron; acetic acid / 4 h / 45 °C / |Inert atmosphere 3: caesium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / toluene / 16 h / |Inert atmosphere; |Reflux 4: potassium carbonate; palladium diacetate; 2-oxo-3,3-dimethyl-butanoic acid / 23 h / 85 °C / |Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / methanol; dichloromethane / 72 h / 20 °C / |Inert atmosphere 6: titanium (IV) isopropoxide / toluene / 15 h / -78 - 20 °C / |Inert atmosphere View Scheme

1: 91 percent / pyridine / 6 h / 20 °C 2: 83 percent / N-bromosuccinimide / CCl4 / 14 h / 20 °C / Photolysis 3: 52 percent / 18-crown-6 / toluene / 20 h / 20 °C View Scheme

1: 91 percent / pyridine / 6 h / 20 °C 2: 83 percent / N-bromosuccinimide / CCl4 / 14 h / 20 °C / Photolysis 3: 52 percent / 18-crown-6 / toluene / 20 h / 20 °C 4: 60.6 percent / hydrazine / CH2Cl2; methanol / 14 h / 20 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 2: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / Reflux View Scheme

1: 1.) aq. NaOH, Hg(OAc)2, 2.) aq. KI, I2 / 1.) AcOH, H2O, 100 deg C, 30 min, 2.) 3 h 2: 96 percent / aq. NaOH, dicyclohexano-18-crown-6 / 3 h / Heating 3: 81 percent / Cu / dimethylformamide / 6 h / 154 °C 4: 72 percent / FeCl3*6H2O, C, N2H4*H2O / methanol / 17 h / Heating 5: 1.) HCl, NaNO2, 2.) KI / 1.) 20 min, 2.) 80 deg C, 2 h 6: 31 percent / Cu2O / 0.17 h / 350 °C 7: 68 percent / BBr3 / benzene; hexane / 40 h / 70 °C View Scheme