sodium hydride in N,N-dimethyl-formamide T=-10 - 20°C;

in benzene Heating;

1.1: 56 percent / TMEDA; s-BuLi; 1,1,2,2-tetrabromoethane / tetrahydrofuran; cyclohexane / -93 - 20 °C 2.1: n-BuLi / diethyl ether; hexane / 0.25 h / -10 - 20 °C 2.2: 21 percent / HCl / ethanol / 12 h / Heating 3.1: 85 percent / NaH / dimethylformamide / -10 - 20 °C 4.1: 84 percent / NiClCpIMes / diethyl ether / 0.17 h / 0 °C View Scheme

1.1: 56 percent / TMEDA; s-BuLi; 1,1,2,2-tetrabromoethane / tetrahydrofuran; cyclohexane / -93 - 20 °C 2.1: n-BuLi / diethyl ether; hexane / 0.25 h / -10 - 20 °C 2.2: 21 percent / HCl / ethanol / 12 h / Heating View Scheme

1.1: 56 percent / TMEDA; s-BuLi; 1,1,2,2-tetrabromoethane / tetrahydrofuran; cyclohexane / -93 - 20 °C 2.1: TMEDA; LDA; triisopropyl borate / H2O2 / tetrahydrofuran / 12 h / 0 - 20 °C 2.2: 57 percent / K2CO3 / acetonitrile / 12 h / Heating 3.1: n-BuLi / diethyl ether; hexane / 0.25 h / -10 - 20 °C 3.2: 31 percent / HCl / methanol / 12 h / Heating View Scheme

K2PO4; bis(acetylacetonate)nickel(II); 1,3-bis-(diphenylphosphino)propane in toluene T=90°C; Suzuki-Miyaura cross-coupling reaction; 24 h;

NiClCpIMes in diethyl ether T=40°C; Grignard cross-coupling reaction; 24 h;

N,N,N',N,-tetramethylethylenediamine; iodine; sec.-butyllithium in tetrahydrofuran; cyclohexane T=-93 - 20°C;