1: 72 percent / dipotassium diazenedicarboxylate / pyridine; methanol; acetic acid / 25 h 2: 1.) tetrakis<triphenylphosphine>-palladium / 1.) benzene, room temp., 15 min, 2.) room temp., overnight 3: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C View Scheme

1: 72 percent / dipotassium diazenedicarboxylate / pyridine; methanol; acetic acid / 25 h 2: 1.) tetrakis<triphenylphosphine>-palladium / 1.) benzene, room temp., 15 min, 2.) room temp., overnight 3: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C 4: pyridine / 1.) 18 h, 0 deg C, 2.) 18 h, room temp. View Scheme

1: 72 percent / dipotassium diazenedicarboxylate / pyridine; methanol; acetic acid / 25 h 2: 1.) tetrakis<triphenylphosphine>-palladium / 1.) benzene, room temp., 15 min, 2.) room temp., overnight 3: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C 4: pyridinium chlorochromate/alumina / CH2Cl2; hexane / 2 h / Ambient temperature View Scheme