Verseifung;

(dihydroxy)isopropylborane; caesium carbonate; triphenylphosphine; norborn-2-ene; palladium diacetate in acetonitrile 20 h; Heating;

bis (triortho-tolylphosphine)palladium(II) chloride in tetrahydrofuran; N,N-dimethyl-formamide T=70°C; cross-coupling; 3 h;

1: 2-bromo-naphthalene With dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate in tetrahydrofuran Negishi Coupling; 0.0833333 h; Schlenk techniqueInert atmosphere; 2: 4-ethoxy-4-oxobutylzinc bromide lithium chloride in tetrahydrofuran T=50°C; Negishi Coupling; 2 h; Schlenk techniqueInert atmosphere;

sulfur T=200°C;

1: H2SO4 2: sulfur / 200 °C View Scheme

pyridine; N,N'-dimethyl-N,N'-propyleneurea; 4,4'-dimethoxy-2,2'-bipyridine; NiI2*3.5H2O; sodium iodide; zinc T=20 - 60°C; 19 h; chemoselective reaction;

1: AlCl3 / nitrobenzene 2: KOH / methanol 3: (i) N2H4*H2O, KOH, diethylene glycol, (ii) (pyrolysis) 4: (i) SOCl2, Py, Et2O, (ii) AlCl3, benzene 5: Zn-Hg, aq. HCl / toluene / Heating View Scheme

diethyl ether; potassium ethanolate Erwaermen des Reaktionsprodukts mit wss. Schwefelsaeure;

ethanol; potassium ethanolate Erhitzen des Reaktionsprodukts mit wss. H2SO4;