1: 60 percent / 1,3-bis(diphenylphosphino)propane, palladium acetate, NaHCO3 / dimethylsulfoxide / 20 h / 85 °C 2: 84 percent / trichlorosilane, Et3N / toluene / 2 h / Heating View Scheme

1.1: bromine / acetic acid / 20 °C 2.1: magnesium / tetrahydrofuran / 2 h / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / ethylene glycol dimethyl ether / 0.5 h 3.2: |Reflux 4.1: boron tribromide / dichloromethane / 20 °C / |Reflux 5.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 20 °C 6.1: Cl2Ni(1,2-bis(diphenylphosphino)ethane) / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Heating 6.2: 40 h / 100 °C View Scheme

1.1: magnesium / tetrahydrofuran / 2 h / |Inert atmosphere 1.2: -78 - 20 °C / |Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0) / ethylene glycol dimethyl ether / 0.5 h 2.2: |Reflux 3.1: boron tribromide / dichloromethane / 20 °C / |Reflux 4.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 20 °C 5.1: Cl2Ni(1,2-bis(diphenylphosphino)ethane) / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Heating 5.2: 40 h / 100 °C View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0) / ethylene glycol dimethyl ether / 0.5 h 1.2: |Reflux 2.1: boron tribromide / dichloromethane / 20 °C / |Reflux 3.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 20 °C 4.1: Cl2Ni(1,2-bis(diphenylphosphino)ethane) / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Heating 4.2: 40 h / 100 °C View Scheme

1: Pd[P(o-tol)3]2; 4-(N,N-dimethlyamino)pyridine; (R,SFc)-Josiphos SL-J003-1 / 1,4-dioxane / 96 h / 80 °C / |Inert atmosphere; |Glovebox 2: 1,3,5-trimethyl-benzene / 150 °C View Scheme