1: benzene 2: lithium alanate; diethyl ether View Scheme

dilithium tetrachlorocuprate in tetrahydrofuran T=0 - 20°C; 5 h;

hexamethyl-distannane in various solvent(s) T=150°C; 48 h; Irradiation;

1.1: Zn; TMSCl; 1,2-dibromoethane / tetrahydrofuran / 30 °C 1.2: 80 percent / 5 percent Ni/C / toluene; dimethylformamide; tetrahydrofuran / 30 h / 20 °C 2.1: 92 percent / H2 / Pd(OH)2/C / ethyl acetate / 6 h / 30 °C / 3040 Torr 3.1: aq. HBr / toluene / 40 h / Heating 4.1: 22 g / aq. NaOH / toluene; methoxybenzene / 6 h / 30 °C View Scheme

a) -78 to 0 deg C, 2 h, b) r.t., 3 h;

bis(acetylacetonate)nickel(II) in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=-25°C; Substitution; 48 h;

1: 1-(phenyl(phenylthio)methylthio)benzene With Cp2Ti[P(OEt)3]2 in tetrahydrofuran T=20°C; complexation; 0.25 h; 2: 5‐iodopentanenitrile in tetrahydrofuran T=20°C; Alkylation; 2 h; 3: With sodium hydroxide Hydrolysis;

sodium iodide in acetone 48 h; RefluxInert atmosphere;

sodium iodide in acetone T=60°C; 12 h; Sealed tube;

N,N,N',N,-tetramethylethylenediamine; ((Me)N2N)Ni-Cl in tetrahydrofuran T=20°C; Kumada-Corriu-Tamao coupling reaction; 2 h; Inert atmosphere;