1.1: Pd(OAc)2; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-(dicyclohexylphosphino)biphenyl / dioxane / 1 h / 80 °C 1.2: 93 percent / Ba(OH)2*8H2O / dioxane; H2O / 1 h / 100 °C 2.1: 64 percent / NaOH / ethanol; H2O / 3 h / Heating View Scheme

in 2,2,2-trifluoroethanol T=150°C; 1 h; microwave irradiation;

triethylamine; 2-dicyclohexylphosphino-1,1'-biphenyl; palladium diacetate T=80°C; 1 h;

triethylamine; 2-dicyclohexylphosphino-1,1'-biphenyl; palladium diacetate T=80°C; 1 h;

1: 91 percent / NaH / dimethylformamide / 1.) 0 deg C, 45 min, 2.) 25 deg C, 3 h 2: 83 percent / Bu3SnH / benzene / 1 h / 70 °C 3: 90 percent / Zn, aq. CH3COOH / tetrahydrofuran / 2 h / 70 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 0.92 h / 0 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C 3.1: manganese; (2,2′-bipyridine)nickel(II) dibromide; trifluoroacetic acid / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere View Scheme

1.1: 88 percent / CuI; Et3N / Pd(PPh3)2Cl2 / 0.67 h / 20 °C 2.1: tBuLi / diethyl ether / -20 °C 2.2: 86 percent / diethyl ether / 5 h / -78 - 20 °C 3.1: 76 percent / NaOEt / ethanol / 7.5 h / Heating 4.1: 72 percent / s-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C 5.1: 74 percent / NaOH / 4 h / 20 °C 6.1: 78 percent / KOH / H2O; ethanol / 2 h / Heating View Scheme

1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C 2: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 1 h / -78 °C 3: toluene-4-sulfonic acid / dichloromethane / 0.17 h / 0 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / |Inert atmosphere 1.2: 4 h / 20 °C / |Inert atmosphere 2.1: manganese; NiBr2bipy; trifluoroacetic acid / N,N-dimethyl-formamide / 50 °C / |Inert atmosphere View Scheme