1: tetrakis(triphenylphosphine) palladium(0); isopropylamine; copper(l) iodide / ethylene glycol dimethyl ether / 3.5 h / 70 °C / |Inert atmosphere 2: hydrogen; palladium 10 on activated carbon / ethyl acetate / 0.75 h / |Inert atmosphere 3: diisobutylaluminium hydride / tetrahydrofuran / 0.25 h / 0 °C 4: dimethyl sulfoxide; sulfur trioxide pyridine complex; triethylamine / dichloromethane / 2 h / 0 °C 5: sodium acetate; hydroxylamine hydrochloride / isopropyl alcohol / 1.5 h / 20 °C 6: Acid orange 52; sodium cyanoborohydride; hydrogenchloride / methanol / 1 h / 20 °C 7: sodium cyanoborohydride / tert-butyl alcohol / 16 h / |Inert atmosphere; |Sealed tube; |Microwave irradiation 8: zinc; trifluoroacetic acid; water / dichloromethane / 20 °C View Scheme

1: 2,6-di-tert-butyl-4-methylphenol; Ti(NEt2)4 / toluene / 24 h / 100 °C 2: ZnCl2 / toluene / 24 h / 100 °C 3: 80 percent / TBAF*3H2O / tetrahydrofuran / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -5 °C 1.2: 90 percent / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 10 h / 20 °C 2.1: HF / acetonitrile / 0.5 h / 20 °C 3.1: 76 percent / 2,2,6,6-tetramethylpiperidine 1-oxyl; NaClO; NaClO2 / acetonitrile; H2O / 5 h / 37 °C / pH 6.86 View Scheme