1: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature 2: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 3: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 2: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 2: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 3: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 4: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 5: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 2: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 3: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 4: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 5: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 6: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 2: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 3: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 4: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 2: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 3: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 4: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 5: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 6: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 7: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 2: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 3: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 2: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 94 percent / p-toluenesulfonic acid, H2O / tetrahydrofuran / 18 h / Ambient temperature 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, 0 deg C, 20 min 3: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h 4: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating 5: 62.4 percent / N-bromosuccinimide (NBS) / CCl4 / 4 h / Ambient temperature 6: 31 percent / salcomine, O2 / dimethylformamide / 20 h / Ambient temperature 7: 97 percent / Pd(PPh3)4, 2 N aq. Na2CO3 / tetrahydrofuran / 0.17 h / 90 °C 8: 80 mg / HClO4 / CH2Cl2 / 2 h / Ambient temperature View Scheme

perchloric acid; ammonium cerium(IV) nitrate 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h; Yield given. Multistep reaction;