1: With n-butyllithium in tetrahydrofuran 2: in tetrahydrofuran; benzene T=80°C; 120 h;

sodium amalgam in tetrahydrofuran T=80°C; 120 h;

tellurium; n-butyllithium 1) in THF, 0 deg C, 2) RT, 3h; Yield given. Multistep reaction. Yields of byproduct given;

1: 74 percent / NaOH / dimethylsulfoxide / 0.5 h / Ambient temperature 2: 86 percent / K2CO3, Bu4NBr / 1,2-dimethoxy-ethane / Ambient temperature View Scheme

sodium amalgam in tetrahydrofuran T=80°C; 120 h;

1.1: n-butyllithium / tetrahydrofuran; methanol; hexane / 0.5 h / -74 °C / |Inert atmosphere; |Automated synthesizer 1.2: 1 h / 15 °C / |Automated synthesizer; |Inert atmosphere 2.1: n-butyllithium / methanol; hexane / 0.5 h / -74 - 0 °C / |Automated synthesizer; |Inert atmosphere 2.2: 2 h / 0 °C / |Automated synthesizer; |Inert atmosphere 3.1: lithium diisopropyl amide / methanol / 2 h / -78 °C / |Inert atmosphere; |Automated synthesizer View Scheme

1: bis(η3-allyl-μ-chloropalladium(II)); [(t-Bu)3PH]BF4; potassium tert-butylate / 1,4-dioxane / 12 h / 80 °C / |Inert atmosphere 2: SIDip*HCl; sodium hydroxide; bis(η3-allyl-μ-chloropalladium(II)) / 1,4-dioxane; water / 12 h / 120 °C / |Inert atmosphere View Scheme