tetrabutyl ammonium fluoride in tetrahydrofuran T=25°C;

1: 3-iodoindole-N-SO2-polystyrene With pinacol borane; triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct in 1,4-dioxane T=80°C; 20 h; 2: thien-2-yl bromide With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=80°C; Suzuki coupling reaction; 24 h; 3: With potassium tert-butylate in tetrahydrofuran T=20°C; 6 h;

indium trifluoromethanesulfonate in 1,4-dioxane; toluene T=100°C; 24 h; Inert atmosphere;

1: 1) t-BuLi, 2) ZnCl2 / 3) PdCl2(Ph3P)2, DIBAH 2: 78 percent / n-Bu4NF / tetrahydrofuran / 25 °C View Scheme

1.1: tBuLi / tetrahydrofuran 1.2: B(OiPr)3 / tetrahydrofuran 1.3: 86 percent / LiOH; aq. Na2CO3; Pd(PPh3)4 / tetrahydrofuran / 20 °C 2.1: tetrabutylammonium fluoride View Scheme

1: in diethyl ether Heating; 2: With lithium aluminium tetrahydride

tetrabutyl ammonium fluoride