hydrogen iodide in tetrahydrofuran T=-5 - 10°C; 2.5 h;

dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate in tetrahydrofuran; water T=50°C; Suzuki-Miyaura cross-coupling reaction; 24 h; Inert atmosphere;

1: H2SO4 / 24 h 2: 1.) n-BuLi / 1.) THF, cyclohexane, -78 deg C, 1 h, 2.) THF, cyclohexane, from -78 to -40 deg C, 4 h 3: 92 percent / 47percent aq. HI / tetrahydrofuran / 2.5 h / -5 - 10 °C View Scheme

1: 1.) n-BuLi / 1.) THF, cyclohexane, -78 deg C, 1 h, 2.) THF, cyclohexane, from -78 to -40 deg C, 4 h 2: 92 percent / 47percent aq. HI / tetrahydrofuran / 2.5 h / -5 - 10 °C View Scheme

1: KHF2 / methanol; water / 20 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / tetrahydrofuran; water / 24 h / 50 °C / Inert atmosphere View Scheme