[(P{(NC5H10)(C6H11)2})2Pd(Cl)2] in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=100°C; Negishi cross-coupling reaction; 18 h; In air;

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; 2 h;

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in acetonitrile T=90°C; Substitution; Suzuki reaction; 2 h;

1: 4-bromophenylacetic acid With tritylchloride-polystyrene resin; N-ethyl-N,N-diisopropylamine in dichloromethane; N,N-dimethyl-formamide T=20°C; 18 h; 2: dihydroxy-thien-2-ylborane With potassium phosphate; phenyl-phospha-adamantane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex in tetrahydrofuran; water T=20°C; solid-phase Suzuki coupling; 15 h; 3: With trifluoroacetic acid in dichloromethane T=20°C; 1.5 h; Further stages.;

sodium carbonate in 1,4-dioxane; water

lithium hydroxide; caesium carbonate; potassium iodide; Merrifield resin; tetrakis(triphenylphosphine) palladium(0) 1.) DMF, 80 deg C, 16 h; 2.) DMF, 60 degC, 24 h; 3.) THF, MeOH, H2O, reflux, 18 h; Yield given. Multistep reaction;

lithium hydroxide; caesium carbonate; potassium iodide; Merrifield resin; tetrakis(triphenylphosphine) palladium(0) 1.) DMF, 80 deg C, 16 h; 2.) DMF, 60 degC, 24 h; 3.) THF, MeOH, H2O, reflux, 18 h; Yield given. Multistep reaction;

1: 85.49 percent / NaBF4, 4M HCl, NaNO2 / 0.33 h / 4 °C 2: 10 percent / KOAc / acetonitrile 3: Na2CO3 / dioxane; H2O View Scheme

1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / N,N-dimethyl-formamide / 90 °C 2: water; lithium hydroxide hydrate / methanol View Scheme

1: sodium nitrite; tetrafluoroboric acid / water 2: Eosin / dimethyl sulfoxide / |Photolysis View Scheme