acetic acid; zinc in water T=90°C; 1.25 h;

indium; [N-butylthiazolium][Br] T=95°C; 14 h; Green chemistry;

1: 2) KMnO4 / 1) Pd(PPh3)4 / 1) dioxane, hexane, reflux, 2) H2O, reflux 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min View Scheme

potassium permanganate; tetrakis(triphenylphosphine) palladium(0) 1) dioxane, hexane, reflux, 2) H2O, reflux; Yield given. Multistep reaction;

dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate in 1,4-dioxane T=80°C; 24 h; Inert atmosphere;

1: sodium hydride / N,N-dimethyl-formamide / 2 h / 40 °C 2: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 16 h / 760.05 Torr View Scheme

1: 2) KMnO4 / 1) Pd(PPh3)4 / 1) dioxane, hexane, reflux, 2) H2O, reflux 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 52 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme