1,3-bis(3-sulfopropyl)-1H-imidazol-3-ium trifluoromethanesulfonate in water T=100°C; Fischer Indole Synthesis; 0.25 h; Microwave irradiationGreen chemistry;

water; 1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran T=20°C; 72 h;

hydrogen; palladium on activated charcoal in methanol T=20°C; P=760 Torr; 0.5 h;

trichloroacetic acid T=100°C; Fischer indole synthesis; 0.0833333 h;

titanium(III) chloride; ammonium acetate in acetone T=20°C; 0.25 h;

1: triphenylarsine; copper(I) iodide / bis(benzonitrile)palladium dichloride / 1-methyl-pyrrolidin-2-one / 48 h / 80 °C 2: 89 percent / hydrogen / palladium on carbon / methanol / 0.5 h / 20 °C / 760 Torr View Scheme

1: 65 percent / iodine; pyridine / CCl4 / 0 - 20 °C 2: triphenylarsine; copper(I) iodide / bis(benzonitrile)palladium dichloride / 1-methyl-pyrrolidin-2-one / 48 h / 80 °C 3: 89 percent / hydrogen / palladium on carbon / methanol / 0.5 h / 20 °C / 760 Torr View Scheme

1: 36 percent / oxygen / palladium diacetate / dimethylsulfoxide / 1 h / 40 °C / 760 Torr 2: 65 percent / iodine; pyridine / CCl4 / 0 - 20 °C 3: triphenylarsine; copper(I) iodide / bis(benzonitrile)palladium dichloride / 1-methyl-pyrrolidin-2-one / 48 h / 80 °C 4: 89 percent / hydrogen / palladium on carbon / methanol / 0.5 h / 20 °C / 760 Torr View Scheme

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 100 percent / triethylamine / tetrahydrofuran; hexane / 1 h / -78 - 20 °C 2.1: 36 percent / oxygen / palladium diacetate / dimethylsulfoxide / 1 h / 40 °C / 760 Torr 3.1: 65 percent / iodine; pyridine / CCl4 / 0 - 20 °C 4.1: triphenylarsine; copper(I) iodide / bis(benzonitrile)palladium dichloride / 1-methyl-pyrrolidin-2-one / 48 h / 80 °C 5.1: 89 percent / hydrogen / palladium on carbon / methanol / 0.5 h / 20 °C / 760 Torr View Scheme

1.1: H2SO4; K2S2O8 / 1.5 h / 20 °C 1.2: 87 percent / KI / H2O 2.1: 78 percent / AgF / H2O 3.1: 87 percent / CO2 / dimethylsulfoxide; CH2Cl2; acetonitrile / -40 - 20 °C 4.1: 89 percent / aq. TiCl3; NH4OAc / acetone / 0.25 h / 20 °C View Scheme