1: 82 percent / methanol / 18 h / Heating 2: 78 percent / DowTherm A / 1 h / 250 °C View Scheme

sodium t-butanolate; Pd PEPPSI-IPr in toluene T=215°C; P=3878.71 Torr; microwave irradiation;

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: dichloromethane / 20 °C / Inert atmosphere 4.1: ruthenium(III) chloride polyhydrate / isopropanol acetate / 15 h / 80 °C / Inert atmosphere 5.1: sodium tetrahydroborate / methanol; water / 20 - 100 °C / Inert atmosphere View Scheme

iodine T=20°C; Inert atmosphere;

1: DMAP / tetrahydrofuran / Heating 2: K2CO3 / methanol / Heating View Scheme

acetic acid in water; 1,2-dichloro-ethane T=80°C; Paal-Knorr reaction;