N,N,N',N,-tetramethylethylenediamine; oxygen; copper(l) chloride in acetone Glazer reaction; 5 h;

copper(l) iodide; N,N,N',N,-tetramethylethylenediamine; oxygen in ethylene glycol dimethyl ether T=55°C; Hay coupling;

1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 °C / |Inert atmosphere 2: Jone's reagent / acetone / 0 °C View Scheme

zirconium sulfophenyl phosphonate in dichloromethane T=20°C; Acetylation; 3 h;

pyridine; acetic anhydride

in pyridine; benzene 2 h; Ambient temperature;

[Ru(N,N-bis[(pyridin-2-yl)methyl][2-(diphenylphosphino)phenyl]methanamine)(CH3COO)][BPh4] in tetrahydrofuran T=80°C; 1 h; Inert atmosphere;

1.1: 96 percent / p-TsOH / diethyl ether / 2 h / 20 °C 2.1: nBuLi / tetrahydrofuran / 2 h / -78 - 0 °C 3.1: 9.95 g / p-TsOH / methanol; H2O / 1 h / 20 °C 4.1: 91 percent / I2; imidazole; PPh3 / toluene / 2 h / 20 °C 5.1: 99 percent / acetonitrile / 16 h / Heating 6.1: KN(SiMe3)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C 6.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C 7.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 8.1: KOH / H2O; methanol / 60 °C 9.1: 2.12 g / TsOH / CH2Cl2 / 0.5 h / 20 °C 10.1: 68 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 8 h / 20 °C 11.1: 92 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C 12.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 13.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 14.1: 81 percent / pyridine / 3 h / Heating 15.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 16.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 17.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 18.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 19.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 20.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 21.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 21.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 22.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 23.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

cis-[Pt(NH3)2(Cl)2] in water T=37°C; 120 h;

cis-[Pt(NH3)2(Cl)2] in water T=37°C; 48 h;