1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 1.25 h / -78 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 60 °C 3.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 20 °C 4.1: ammonium hydroxide / tetrahydrofuran / 48 h / -78 - 20 °C / |Sealed tube 5.1: triethylamine; iodine / methanol / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1,10-phenanthroline; caesium carbonate; copper(l) iodide in toluene T=110°C; Ullman coupling; 12 h;

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 16 h / -78 - 35 °C 2.1: phenyl isocyanate; triethylamine / toluene / 4 h / 20 - 80 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 °C 4.1: tetrachloromethane; triphenylphosphine / dichloromethane / 0.33 h / 20 - 50 °C 5.1: lithium hydroxide hydrate; water / tetrahydrofuran / 19 h / 20 °C View Scheme

1: 4-(tert-butyldimethylsiloxymethyl)iodobenzene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.75 h; 2: ethyl-α,α,α-trifluoroacetate in tetrahydrofuran; hexane T=-78°C; 1.25 h;

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 1.25 h / -78 °C 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 60 °C 3.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 20 °C 4.1: ammonium hydroxide / tetrahydrofuran / 48 h / -78 - 20 °C / |Sealed tube View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT<br />2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -78 deg C, 15 min, b) from -78 deg C to RT<br />3: 95 percent / iodine monochloride / CCl₄ / 1.) RT, 30 min, 2.) reflux, 1 h<br />4: oxalyl chloride, DMF / toluene / 1 h / Ambient temperature<br />5: LiCl, NaBH₄ / 1,2-dimethoxy-ethane / 1 h<br />6: 97.7 percent / (4-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: oxalyl chloride, DMF / toluene / 1 h / Ambient temperature<br />2: LiCl, NaBH₄ / 1,2-dimethoxy-ethane / 1 h<br />3: 97.7 percent / (4-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: LiCl, NaBH₄ / 1,2-dimethoxy-ethane / 1 h<br />2: 97.7 percent / (4-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature<br /> <br /> &nbsp;