sodium perborate in acetic acid T=25°C; 2 h;

1: 100 percent / hydrogen / platinum(IV) oxide / ethyl acetate / 4.5 h 2: nitrogen tetroxide / acetonitrile / 1.25 h / -20 °C 3: sodium iodide / acetonitrile / -20 - 20 °C 4: 92 percent / trifluoroacetic acid / CH2Cl2 / 23 h / 20 °C View Scheme

silica-supported sulfuric acid T=20°C; 0.25 h; Neat (no solvent); chemoselective reaction;

With  hydrogen; platinum(IV) oxide in  ethyl acetate 4.5 h;