1: 4,4’-dibromo-2,2’-diiodobiphenyl With tert.-butyl lithium in tetrahydrofuran; hexane T=-90°C; 0.5 h; Inert atmosphere; 2: di-(n-octyl)dichlorosilane in tetrahydrofuran; hexane T=-90 - 20°C; Inert atmosphere;

1.1: 92 percent / tin; HCl / ethanol; H2O / 2 h / 100 °C 2.1: HCl; NaNO2 / H2O / 30 h / 0 °C 2.2: 28 percent / KI / H2O / -5 - 20 °C 3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 70 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme

1.1: HCl; NaNO2 / H2O / 30 h / 0 °C 1.2: 28 percent / KI / H2O / -5 - 20 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 70 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme

1.1: copper / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere 2.1: hydrogenchloride; tin / ethanol; water / 2 h / 100 °C / Inert atmosphere 3.1: hydrogenchloride; sodium nitrite / water; acetonitrile / 1 h / -10 - -5 °C / Inert atmosphere 3.2: 20 h / 80 °C / Inert atmosphere 4.1: tert.-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -90 °C / Inert atmosphere 4.2: -90 - 20 °C / Inert atmosphere View Scheme

1: 3,7-dibromo-5,5-di-n-octyl-dibenzo[b,d]silole With tert.-butyl lithium in tetrahydrofuran; pentane T=-78°C; 0.25 h; 2: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran; pentane T=25°C; Further stages.;

potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane T=80°C; 5.5 h; Inert atmosphere;