N,N,N',N,-tetramethylethylenediamine; PdCl2(amphos)2; zinc in water T=20°C; Negishi-like cross-coupling; 24 h; Inert atmosphere;

1: 100 percent / H2 / 10percent Pd-C / hexane; triethylamine / 24 h 2: 1.) BCl3, 2.) 0.5 M Na2CO3, 3.) Pd(PPh3)4, 2 M Na2CO3 / 1.) CH2Cl2, -78 deg C, 2 h; -78 deg C to 0 deg C, 8 h, 3.) MeOH, toluene, 110 deg C, 2 h View Scheme

[1,3-bis(diphenylphosphino) propane] dichloronickel(II)

3,4-Dibromo-thiophene; tetrakis(triphenylphosphine) palladium(0); boron trichloride; sodium carbonate 1.) CH2Cl2, -78 deg C, 2 h; -78 deg C to 0 deg C, 8 h, 3.) MeOH, toluene, 110 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

tetrakis(triphenylphosphine) palladium(0); boron trichloride; sodium carbonate 1.) CH2Cl2, -78 deg C, 2 h; -78 deg C to 0 deg C, 8 h, 3.) MeOH, toluene, 110 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;