zinc dibromide; tetrakis(triphenylphosphine) palladium(0) T=50°C; 12 h;

palladium on activated charcoal in various solvent(s) 3 h; Heating;

palladium diacetate; triethylamine; triphenylphosphine in N,N-dimethyl-formamide T=80°C; intramolecular Heck olefination; 16 h;

1: 1) lithium diisopropylamide, hexamethyl phosphoramide / 1) THF, 0 deg C, 20 min; 2) THF, a) 25 deg C, 1 h, b) heating, 2 h 2: 1.) phosphorus pentachloride; 2.) aluminum chloride / 1.) benzene, reflux, 10 min; 2.) reflux, 30 min 3: 2.) conc. hydrochloric acid / 1.) ether, reflux, 12 h; 2.) methanol, reflux, 3 h 4: 93 percent / palladium on carbon / various solvent(s) / 3 h / Heating View Scheme

1: 2.) conc. hydrochloric acid / 1.) ether, reflux, 12 h; 2.) methanol, reflux, 3 h 2: 93 percent / palladium on carbon / various solvent(s) / 3 h / Heating View Scheme

1: 1.) phosphorus pentachloride; 2.) aluminum chloride / 1.) benzene, reflux, 10 min; 2.) reflux, 30 min 2: 2.) conc. hydrochloric acid / 1.) ether, reflux, 12 h; 2.) methanol, reflux, 3 h 3: 93 percent / palladium on carbon / various solvent(s) / 3 h / Heating View Scheme

9,10-anthracenedicarbonitrile in acetonitrile 0.5 h; Irradiation;