potassium hydroxide in methanol; benzene T=20°C; 3 h;

n-butyllithium in tetrahydrofuran 1.) -78 deg C, 1 h, 2.) r.t., 1 h;

1: Pd(PPh3)4; CuI 2: 100 percent / KOH / methanol; benzene / 3 h / 20 °C View Scheme

1: 65 percent / aq. NaNO2; HCl; KI / -5 - 0 °C 2: CuI; Et3N / Pd(PPh3)2Cl2 / 4 h / 50 °C 3: 3.4 g / NaOH / methanol / 4 h / 20 °C View Scheme

1.1: bromine; neutral alumina / 0.02 h 1.2: 5.26 g / copper(I) iodide; triphenylphosphine; triethylamine / bis(triphenylphosphine)palladium(II) dichloride / tetrahydrofuran / 72 h / 85 °C 2.1: potassium carbonate / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

1: 1.) Ph3P, Zn / 1.) CH2Cl2, r.t., 48 h, 2.) 2 h 2: 89 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) r.t., 1 h View Scheme

1: [1,3-bis(diphenylphosphino) propane] dichloronickel(II) / diethyl ether / 24 h / Reflux 2: potassium carbonate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere View Scheme

1: [1,3-bis(diphenylphosphino) propane] dichloronickel(II) / diethyl ether / 24 h / Reflux 2: potassium carbonate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere View Scheme

1: AlCl3, aluminium chloride / 1 h / 50 °C 2: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 210 °C / 760.05 Torr 3: copper(l) iodide; palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; diisopropylamine; triphenylphosphine / 16 h / 90 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere View Scheme

1: copper(l) iodide; palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; diisopropylamine; triphenylphosphine / 16 h / 90 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere View Scheme