toluene-4-sulfonic acid in water; acetone T=20°C; 1.5 h;

oxygen; palladium diacetate in dichloromethane; dimethyl sulfoxide T=35°C; Product distribution / selectivity;

1: p-TSA 2: pyridine*HBr3 3: t-BuOK / dimethylsulfoxide 4: p-TSA / acetone; H2O View Scheme

1: 97 percent / K2CO3; diisopropylethylamine / acetone / 72 h / 20 °C 2: 52 percent / pTsOH / acetone; H2O / 1.5 h / 20 °C View Scheme

1: potassium carbonate / dichloromethane; methanol / 16 h / Reflux 2: triethylamine / dichloromethane / 1 h / 20 °C 3: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C View Scheme

1: pyridine*HBr3 2: t-BuOK / dimethylsulfoxide 3: p-TSA / acetone; H2O View Scheme

1: t-BuOK / dimethylsulfoxide 2: p-TSA / acetone; H2O View Scheme

1.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C 1.2: 2 h / 0 - 8 °C 2.1: pyridine / 4-(N,N-dimethlyamino)pyridine / 2 h / 20 °C 3.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C 4.1: hydrogen / palladium 10 on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr 5.1: potassium carbonate; methanol / 4 h / 20 °C View Scheme