hydrogenchloride; iron(III) chloride; iron in ethanol; water 3 h; Heating;

palladium diacetate; caesium carbonate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in 1,4-dioxane T=80°C; 16 h; Inert atmosphere; chemoselective reaction;

potassium phosphate; [Pd(η3-1-Ph-allyl)(μ-Cl)]2; (Mor-DalPhos) in 1,4-dioxane; tert-butyl alcohol T=90°C; Inert atmosphereGlovebox;

potassium hydroxide in methanol; water 2 h; Heating;

1: 87 percent / NH4OAc / 7 h / 105 °C 2: 65 percent / H2, glacial AcOH / Raney Ni / 15 h / 25 °C View Scheme

1: 96 percent / potassium carbonate, sodium iodide / acetone / 24 h / Heating 2: 99 percent / 5 h / 190 °C 3: 93 percent / potassium carbonate / acetone / 16 h / Heating 4: 1.) ozone, 2.) zinc, 50percent aq. acetic acid / 1.) ethyl acetate, 0 deg C, 2.) ethyl acetate, reflux, 1 h 5: 98 percent / H2 / 10percent Pd/C / ethyl acetate 6: 78 percent / KOH / H2O; methanol / 2 h / Heating View Scheme

1: 99 percent / 5 h / 190 °C 2: 93 percent / potassium carbonate / acetone / 16 h / Heating 3: 1.) ozone, 2.) zinc, 50percent aq. acetic acid / 1.) ethyl acetate, 0 deg C, 2.) ethyl acetate, reflux, 1 h 4: 98 percent / H2 / 10percent Pd/C / ethyl acetate 5: 78 percent / KOH / H2O; methanol / 2 h / Heating View Scheme

1: 93 percent / potassium carbonate / acetone / 16 h / Heating 2: 1.) ozone, 2.) zinc, 50percent aq. acetic acid / 1.) ethyl acetate, 0 deg C, 2.) ethyl acetate, reflux, 1 h 3: 98 percent / H2 / 10percent Pd/C / ethyl acetate 4: 78 percent / KOH / H2O; methanol / 2 h / Heating View Scheme