1: trimethylsilylacetylene With ethylmagnesium bromide 48 h; Reflux; 2: 1,8-cichloro-anthracene Kumada coupling reaction; 48 h; Reflux;

1: 68.4 percent / N-methylpyrrolidinone / 67 h / Heating 2: 81 percent / diisobutylaluminum hydride (DIBAL-H) / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 1.) zinc bromide, lithium / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, 0 deg C, 2 h, ultrasonic activation; 2.) THF, room temperature, 3 h 2: sodium, ammonia / methanol; dioxane / 2 h / 80 °C / Heating View Scheme

bis(acetylacetonate)nickel(II) in tetrahydrofuran 3 h;

1: 75 percent / PPh3 / Ni(acac)2 / tetrahydrofuran / Heating 2: 61 percent / K2CO3 / methanol; tetrahydrofuran View Scheme

1: quinoline / Heating 2: KOH / ethane-1,2-diol / 150 - 155 °C View Scheme