1: 3,4,5-trimethoxyphenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; triphenylphosphine in toluene T=20°C; Suzuki coupling; Inert atmosphere; 2: 3,4-Dibromo-thiophene in toluene Suzuki coupling; Inert atmosphere; 3: With sodium carbonate in toluene T=20°C; Inert atmosphereReflux;

5 palladium on charcoal in ethanol T=60°C; 22 h; regioselective reaction;

1: 80 percent / N-bromosuccinimide / CH2Cl2; acetic acid / 0 - 20 °C 2: 81 percent / bromine / CH2Cl2 / 8 h / 50 °C 3: 92 percent / n-BuLi / diethyl ether / 2 h / -70 °C View Scheme

1: 81 percent / bromine / CH2Cl2 / 8 h / 50 °C 2: 92 percent / n-BuLi / diethyl ether / 2 h / -70 °C View Scheme

manganese; tetrakis(triphenylphosphine) palladium(0); ethylene dibromide 1.) THF, 5 h, room t., 2.) THF, 0 deg C to room t., 20 min, 3.) THF, room t., 30 min; Yield given. Multistep reaction;

1: 3-bromo-4-phenylthiophene With n-butyllithium in diethyl ether T=-78°C; 0.5 h; Inert atmosphere; 2: carbon dioxide in diethyl ether T=-78°C; 1 h; Inert atmosphere; 3: With hydrogenchloride in water

1.1: n-butyllithium / diethyl ether / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: polyphosphoric acid / 200 °C View Scheme