thiophenol radical source;

1: 1.) (C2H5)2ZrHCl, 2.) I2 / 1.) benzene, 2.) benzene 2: 1.) (C2H5)2ZrHCl, 2.) Pd(PPh3)4 / 1.) benzene, 2.) THF 3: aq. acid / methanol 4: PCC / CH2Cl2 View Scheme

1: 48 percent / HMPA, LiHMDS / tetrahydrofuran / 0.17 h / -78 °C 2: 50 percent / HMPA, LiHMDS / tetrahydrofuran / 0.17 h / -78 °C 3: 92 percent / PPTS / methanol; CH2Cl2 / 2 h / 40 °C 4: 94 percent / K2CO3 / aq. ethanol / 0.5 h / 125 °C 5: 68 percent / PCC on alumina / CH2Cl2; hexane / 15 h / Ambient temperature View Scheme

1: 94 percent / K2CO3 / aq. ethanol / 0.5 h / 125 °C 2: 68 percent / PCC on alumina / CH2Cl2; hexane / 15 h / Ambient temperature View Scheme

1: 50 percent / HMPA, LiHMDS / tetrahydrofuran / 0.17 h / -78 °C 2: 92 percent / PPTS / methanol; CH2Cl2 / 2 h / 40 °C 3: 94 percent / K2CO3 / aq. ethanol / 0.5 h / 125 °C 4: 68 percent / PCC on alumina / CH2Cl2; hexane / 15 h / Ambient temperature View Scheme

1: 92 percent / PPTS / methanol; CH2Cl2 / 2 h / 40 °C 2: 94 percent / K2CO3 / aq. ethanol / 0.5 h / 125 °C 3: 68 percent / PCC on alumina / CH2Cl2; hexane / 15 h / Ambient temperature View Scheme

1: 1.) Li/NH3 liq. / 2.) DMSO, gentle warming, 2h 2: 98 percent / morpholine, iodine / benzene / 24 h / 45 °C 3: 72 percent / dipotassium diazenedicarboxylate / pyridine; methanol; acetic acid / 25 h 4: 1.) tetrakis<triphenylphosphine>-palladium / 1.) benzene, room temp., 15 min, 2.) room temp., overnight 5: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C 6: pyridinium chlorochromate/alumina / CH2Cl2; hexane / 2 h / Ambient temperature 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

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

1: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C 2: pyridinium chlorochromate/alumina / CH2Cl2; hexane / 2 h / Ambient temperature View Scheme