1: With iodine; magnesium in tetrahydrofuran 2: With [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in tetrahydrofuran

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in diethyl ether T=-10 - 20°C; 5.5 h;

sodium sulfide in 2-methoxy-ethanol Heating;

[1,3-bis(diphenylphosphino) propane] dichloronickel(II) in diethyl ether 16 h; Heating;

1: 74 percent / CuCl, N,N,N',N'-tetramethylethylenediamine, air / 1,2-dimethoxy-ethane / 1 h / 30 - 35 °C 2: 94.6 percent / Na2S*9H2O / 2-methoxy-ethanol / Heating View Scheme

1: 1.) PPh3 / 1.) CH2Cl2, 0 deg C, 5 min, 2.) RT, 1 h 2: 48 percent / n-BuLi / diethyl ether / 1.) -78, 1 h, 2.) RT, 1 h 3: 74 percent / CuCl, N,N,N',N'-tetramethylethylenediamine, air / 1,2-dimethoxy-ethane / 1 h / 30 - 35 °C 4: 94.6 percent / Na2S*9H2O / 2-methoxy-ethanol / Heating View Scheme

1: 48 percent / n-BuLi / diethyl ether / 1.) -78, 1 h, 2.) RT, 1 h 2: 74 percent / CuCl, N,N,N',N'-tetramethylethylenediamine, air / 1,2-dimethoxy-ethane / 1 h / 30 - 35 °C 3: 94.6 percent / Na2S*9H2O / 2-methoxy-ethanol / Heating View Scheme