1: 1.) 9-H-9-BBN, 2.) NaOMe, PdCl2(dppf) / 1.) THF, rt, 2 h, 2.) THF, reflux, 1 h 2: 95 percent / KOH / dimethylsulfoxide; H2O / 1 h / 80 °C View Scheme

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / acetonitrile / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation 2: palladium 10 on activated carbon; hydrogen / methanol / 40 °C / 2280.15 Torr / Autoclave 3: potassium hydroxide / tetrahydrofuran; water / 55 °C View Scheme

1.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 - 0 °C 1.2: 85 percent / MeI / tetrahydrofuran; diethyl ether / 0.17 h / 0 °C 2.1: 78 percent / N-bromosuccinimide; AIBN / CCl4 / 2 h / Heating View Scheme

bis-triphenylphosphine-palladium(II) chloride; lithium chloride in N,N-dimethyl-formamide T=100°C; Stille coupling; 12 h;

1.1: copper(l) iodide; methyllithium / tetrahydrofuran; diethyl ether / 1 h / -78 °C 1.2: 0.17 h / 20 °C 2.1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 4 h / |Reflux 3.1: copper dilithium tetrachloride / tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 4.1: potassium carbonate / methanol / 20 °C View Scheme