1: 73 percent / H2 / 20percent Pd(OH)2-C 2: 1.) NaNO2, hydrogen chloride, 2.) KI 3: 99 percent / NaOMe / methanol View Scheme

1: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 2: 1.) NaNO2, HCl (2N) 2.) CuCl, HCl / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 3: 79 percent / aq. NaOH (40percent) / methanol / 0.25 h / Heating View Scheme

1: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 2: 1.) NaNO2, HCl (2N) 2.) CuCN, NaCN / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 1 h; 94 deg C, 5 min 3: 91.8 percent / aq. NaOH (40percent) / methanol / 0.17 h / Heating View Scheme

1: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 2: 1.)NaNO2, HCl / 1.) water and methanol, 5 deg C, 5 min, 2.) water, 97 deg C, 50 min 3: 74.9 percent / aq. NaOH (40percent) / methanol / 10 h / Heating View Scheme

1: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 2: 1.) NaNO2, HCl (2N) 2.) KI / 1.) water, 5 deg C, 15 min, 2.) water, room temp., 30 min; 85 deg C, 5 min 3: 20.9 percent / triphenylphosphine, triethylamine / palladium acetate / acetonitrile / 13 h / 110 - 115 °C View Scheme

Multi-step reaction with 3 steps 1: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature2: 1.) NaNO2, HCl, 2.) NaBF4 / 1.) water,5 deg C, 20 min. 2.) water, 0 deg C, 20 min; room temp., 30 min3: 50.6 percent / SiO2 / neat (no solvent) / 0.33 h / 175 - 180 °C  

Multi-step reaction with 2 steps 1: 73 percent / H2 / 20percent Pd(OH)2-C2: 1.) NaNO2, hydrogen chloride, 2.) KI  

Multi-step reaction with 2 steps 1: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature2: 1.) NaNO2, HBr (4.7percent) 2.) CuBr, conc. HBr / 1.) water, 5 deg C, 15 min, 2.) water, room temp., 2 h; 94 deg C, 5 min