1: With 1,1,1,2,2,2-hexabutyl-distannane in benzene Metallation; 1 h; Heatingirradiation; 2: With 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene Cyclization; 1.5 h; Heating;

1: With AgNTf2 in toluene T=20°C; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water; toluene T=20°C; 0.75 h; Inert atmosphere;

T=315°C;

1.1: NaH / dimethylformamide / 0.5 h / 0 °C 1.2: dimethylformamide / 16 h / 20 °C 2.1: LiI / dimethylformamide / 5 h / Heating 3.1: hexamethyldisilazane / CH2Cl2 / 0.67 h / 0 - 20 °C 4.1: NaI, m-CPBA / CH2Cl2; tetrahydrofuran / 0.5 h / 0 °C 5.1: (Bu3Sn)2 / benzene / 1 h / Heating; irradiation 5.2: 87 percent / 2,2'-azobisisobutyronitrile, Bu3SnH / benzene / 1.5 h / Heating View Scheme

1: With AgNTf2 in dichloromethane T=20°C; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water T=20°C; 0.75 h; Inert atmosphere;

1.1: LiI / dimethylformamide / 5 h / Heating 2.1: hexamethyldisilazane / CH2Cl2 / 0.67 h / 0 - 20 °C 3.1: NaI, m-CPBA / CH2Cl2; tetrahydrofuran / 0.5 h / 0 °C 4.1: (Bu3Sn)2 / benzene / 1 h / Heating; irradiation 4.2: 87 percent / 2,2'-azobisisobutyronitrile, Bu3SnH / benzene / 1.5 h / Heating View Scheme

1: 8.25 g / K2CO3 / acetone / 19 h / Heating 2: 87 percent / LiI / dimethylformamide / 0.83 h / 150 °C 3: 1.) Et33N, NaI, trimethylsilyl chloride, 2.) HgCl2, hexamethyldisilazane, 3.) NaI, aq. HCl / 1) CH3CN, rt, 45 min; 2) CH2Cl2, THF, rt, 120 min; 3) CH2Cl2, THF, 0 deg C, 15 h View Scheme

1: 87 percent / LiI / dimethylformamide / 0.83 h / 150 °C 2: 1.) Et33N, NaI, trimethylsilyl chloride, 2.) HgCl2, hexamethyldisilazane, 3.) NaI, aq. HCl / 1) CH3CN, rt, 45 min; 2) CH2Cl2, THF, rt, 120 min; 3) CH2Cl2, THF, 0 deg C, 15 h View Scheme

1: n-BuLi / 0 °C 2: HCl, H2O / 1 h 3: 1.) HMDS, TMSI, 2.) NaI, MCPBA / 1.) CH2Cl2, 2.) THF 4: 1.) (Bu3Sn)2, 2.) Bu3SnH, AIBN / 1.) C6H6, irradiation, 1.5 h, 2.) C6H6 View Scheme

1: 90 percent / TFA 2: n-BuLi / 0 °C 3: HCl, H2O / 1 h 4: 1.) HMDS, TMSI, 2.) NaI, MCPBA / 1.) CH2Cl2, 2.) THF 5: 1.) (Bu3Sn)2, 2.) Bu3SnH, AIBN / 1.) C6H6, irradiation, 1.5 h, 2.) C6H6 View Scheme