hydrogen; palladium on activated charcoal in acetone P=2574.3 Torr; 6 h; Ambient temperature;

mercury(II) diacetate; sodium acetate in acetic acid T=120 - 125°C; 2-3 h;

1: PBr3 / diethyl ether 2: triphenylphosphine 3: sodium ethoxide 4: H2 / Pd-C / ethyl acetate 5: pyridine hydrobromide View Scheme

1: 1.) NaH / 1.) DMSO, r.t., 10 min, 2.) r.t., 1 h 2: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 3: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 4: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 93 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 4: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 5: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 6: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 7: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme

1: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 2: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 3: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme

1: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 2: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 3: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme

1: 88 percent / N-bromosuccinimide, triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature 2: 75 percent / 2 h / 140 °C 3: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 4: 93 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 5: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 6: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 7: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 8: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme

1: 93 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 3: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 4: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 5: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme

1: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 2: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme