n-butyllithium; boron trifluoride diethyl etherate in tetrahydrofuran T=-78°C; 1 h;

boron trifluoride diethyl etherate in tetrahydrofuran; hexane T=-78°C; 2 h;

/BRN= 1740549/;

water; Hg(OTf)2 in acetonitrile T=20°C; 0.166667 h; regioselective reaction;

1: 44 percent / 80percent NaH, 1,3-propanediamine / 16 h / 60 °C 2: p-toluenesulfonic acid monohydrate / 0.67 h / Ambient temperature 3: 1.) 1.55M nBuLi / 1.) THF, hexane, -78 deg C, 5 min; -30 deg C, 5 min, 2.) THF, hexane, -78 deg C, 15 min; r.t., 20 min 4: p-toluenesulfonic acid monohydrate / methanol / 0.08 h / Heating 5: 99 percent / H2 / 5percent Pd/BaSO4 / pyridine; quinoline / 0.67 h / 750.06 Torr 6: 72 percent / diphenyldisulfide / cyclohexane / 1.83 h / Irradiation 7: 99 percent / 2N KOH / ethanol / 0.5 h / Heating View Scheme