palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl in toluene 20 h; Heating;

triethylamine in N,N-dimethyl-formamide T=110°C; Dehydrochlorination; 6 h;

1.1: potassium carbonate / acetone / Reflux 2.1: hydrogenchloride; iron / ethanol; water / Reflux 3.1: sulfuric acid / tetrahydrofuran / 0 °C 3.2: 0.5 h / 0 °C 3.3: 3 h / 0 °C / Reflux 4.1: copper(l) iodide; copper; potassium carbonate / 1-methyl-pyrrolidin-2-one / 40 h / 160 °C View Scheme

1.1: hydrogenchloride; iron / ethanol; water / Reflux 2.1: sulfuric acid / tetrahydrofuran / 0 °C 2.2: 0.5 h / 0 °C 2.3: 3 h / 0 °C / Reflux 3.1: copper(l) iodide; copper; potassium carbonate / 1-methyl-pyrrolidin-2-one / 40 h / 160 °C View Scheme

1.1: sulfuric acid / tetrahydrofuran / 0 °C 1.2: 0.5 h / 0 °C 1.3: 3 h / 0 °C / Reflux 2.1: copper(l) iodide; copper; potassium carbonate / 1-methyl-pyrrolidin-2-one / 40 h / 160 °C View Scheme

1: 62 percent / TiCl4 / toluene / 48 h / 20 °C 2: (CH3CH2)3N / dimethylformamide / 6 h / 110 °C View Scheme

in methanol; chloroacetyl chloride

in isopropyl alcohol; toluene T=80 - 100°C; Substitution; 4 h;

1: 1.5 h / 105 °C 2: 0.35 g / AlCl3 / 2 h / 150 °C 3: 38 percent / AlCl3 / 4 h / 200 - 210 °C View Scheme

1: benzene / 2 h / Ambient temperature 2: AlCl3 / various solvent(s) / 20 h / Ambient temperature 3: 1 N NaOH / ethanol; H2O / 0.17 h / Heating 4: hydrazine hydrate, NaOCH3 / 2-methoxy-ethanol / 1.) from 60 deg C to 150 deg C, 2.) 150 deg C, 1 h 5: pyridine hydrochloride / 3 h / 180 °C 6: NaOH, KOH / butan-1-ol / 24 h / Heating View Scheme