1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 67 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 57 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 5: 90 percent / aq. HBr / 72 h / 110 °C View Scheme

1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 63 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation View Scheme

1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 67 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 31 percent / Me6Sn2 / benzene / 9 h / 80 °C / Irradiation View Scheme

1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 5: 82 percent / aq. HBr / 72 h / 110 °C View Scheme

1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation View Scheme

1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 58 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 5: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 67 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 57 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 5: 90 percent / aq. HBr / 72 h / 110 °C View Scheme

1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature 2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C 3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h 4: 53 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation 5: 76 percent / TFA / 10 h / Heating View Scheme