potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine in tetrahydrofuran T=60°C; Suzuki coupling; 6 h;

sulfuric acid; iodine; periodic acid in acetic acid T=70°C; 2 h;

1: 1.) n-BuLi / 1.) THF, -78 deg C, 5 min, 2.) THF, -78 deg C, 5 min 2: 93 percent / n-Bu4NI / dimethylformamide / 24 h / 80 °C 3: 100 percent / Dibal-H / toluene / 2 h / -78 deg C -> 0 deg C 4: 95 percent / HCl(g) 5: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) ICl, Et3N / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

1: 93 percent / n-Bu4NI / dimethylformamide / 24 h / 80 °C 2: 100 percent / Dibal-H / toluene / 2 h / -78 deg C -> 0 deg C 3: 95 percent / HCl(g) 4: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) ICl, Et3N / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

1: 100 percent / Dibal-H / toluene / 2 h / -78 deg C -> 0 deg C 2: 95 percent / HCl(g) 3: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) ICl, Et3N / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

1: 95 percent / HCl(g) 2: 1.) Wang resin, Huenig's base, 2.) 3percent Pd(PPh3)4, 2M Na2CO3, 3.) ICl, Et3N / 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h View Scheme

tetrakis(triphenylphosphine) palladium(0); iodine cloride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; Wang resin 1.) DMF, 40-50 deg C, 2.) DME, reflux, 3.) DMF, 80-90 deg C, 24 h; Yield given. Multistep reaction;

pyridine; palladium diacetate; potassium carbonate T=100°C; 3 h; Ionic liquid;