palladium diacetate; oxygen; sodium acetate in dimethyl sulfoxide T=80°C; 72 h;

pyridine in chloroform T=0 - 20°C;

pyridine; sodium hydroxide in dichloromethane

1: 66 percent / BF3*Et2O / xylene / 2 h / 180 °C 2: 90 percent / pyridine / CH2Cl2 / 0 - 20 °C View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C 2: boron trifluoride diethyl etherate / xylenes / 6 h / 180 °C 3: pyridine / dichloromethane / 24 h / 20 °C View Scheme

1.1: potassium carbonate / acetonitrile / 24 h / 80 °C 2.1: isopropylmagnesium chloride lithium chloride complex / tetrahydrofuran / 0.5 h / -10 °C / |Inert atmosphere 2.2: -10 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 16 h / 35 °C / |Inert atmosphere; |Sealed tube 4.1: pyridine / dichloromethane / 0 - 20 °C View Scheme

magnesium 1) THF, rt, 30 min; 2) THF, rt, 1 h; Yield given. Multistep reaction;