1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 °C / Inert atmosphere 2.1: methanol / Inert atmosphere 3.1: Ni(PCy3)2Cl2; K3PO4; 1,1,3,3-tetramethyldisiloxane / toluene / 15 h / 120 °C / Inert atmosphere View Scheme

zirconocene dichloride in tetrahydrofuran T=20°C; Inert atmosphere;

N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) THF, -78 deg C, 1 h, 2.) to room temp., 8 to 12 h; Yield given. Multistep reaction. Yields of byproduct given;

potassium phosphate; Ni(PCy3)2Cl2 in toluene T=130°C; Suzuki-Miyaura coupling reaction; 24 h; Inert atmosphere;

1: 1) BuLi, 2) ZnCl2, 3) PdCl2(PPh3)2, DIBAL-H / 1) THF, -78 deg C, 2) THF, -78 deg C, 3) THF, 0 deg C to RT 2: 84 percent / NaH / tetrahydrofuran / Heating 3: 85 percent / TFA / toluene / 1 h / Heating View Scheme

1.1: N,N,N',N'-tetramethylethylenediamine; sec-BuLi / tetrahydrofuran / 1.5 h / -78 °C 1.2: I2 / tetrahydrofuran / 0.5 h / -78 °C 2.1: 2N aq. NaOH / methanol / 96 h / Heating View Scheme

sodium t-butanolate; bis(1,5-cyclooctadiene)nickel (0); SIDip*HCl in 1,4-dioxane T=80°C; 3 h; Inert atmosphere;

1: 4-methoxy-phenol With sodium hydride in ethylene glycol dimethyl ether; mineral oil T=0 - 23°C; 0.166667 h; 2: N,N-diethyl carbamoyl chloride in ethylene glycol dimethyl ether; mineral oil T=23°C; 11 h;

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 1.2: 1.17 h / -78 °C / Inert atmosphere 2.1: Ni(PCy3)2Cl2; K3PO4; 1,1,3,3-tetramethyldisiloxane / toluene / 15 h / 120 °C / Inert atmosphere View Scheme