p-benozquinone; copper dichloride; palladium dichloride in 1,4-dioxane T=80°C; 12 h;

tetrabutylammomium bromide; triphenylphosphine; palladium diacetate in acetonitrile T=80°C; 3 h;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / cooling 1.2: 60 percent / hexane; tetrahydrofuran / 0.5 h / 20 °C 2.1: thionyl chloride / 1 h / 65 °C 3.1: 95 percent / triethylamine / CH2Cl2 4.1: 65 percent / CuCl2; benzoquinone / PdCl2 / dioxane / 12 h / 80 °C View Scheme

1.1: diethyl zinc; trifluoroacetic acid / CH2Cl2; hexane / 20 h / cooling 1.2: 93 percent / CH2Cl2; hexane / 0.5 h / cooling 2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / cooling 2.2: 60 percent / hexane; tetrahydrofuran / 0.5 h / 20 °C 3.1: thionyl chloride / 1 h / 65 °C 4.1: 95 percent / triethylamine / CH2Cl2 5.1: 65 percent / CuCl2; benzoquinone / PdCl2 / dioxane / 12 h / 80 °C View Scheme

1: thionyl chloride / 1 h / 65 °C 2: 95 percent / triethylamine / CH2Cl2 3: 65 percent / CuCl2; benzoquinone / PdCl2 / dioxane / 12 h / 80 °C View Scheme

1.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -80 °C 1.2: 71 percent / tetrahydrofuran; pentane / 12 h / 20 °C 2.1: 75 percent / Et3N / PdPhCH2Cl(Ph3P)2 / tetrahydrofuran / Heating View Scheme

1.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -80 °C 1.2: 71 percent / tetrahydrofuran; pentane / 12 h / 20 °C 2.1: 75 percent / Et3N / PdPhCH2Cl(Ph3P)2 / tetrahydrofuran / Heating View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 2.16 h / 0 - 20 °C / Inert atmosphere 1.2: 24 h / 0 - 20 °C / Inert atmosphere 2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 5 h / Reflux; Inert atmosphere 3.1: dichloromethane / 0.08 h / 0 °C / Inert atmosphere 3.2: 12 h / 0 - 20 °C / Inert atmosphere 4.1: dichloro bis(acetonitrile) palladium(II); oxygen; triethylamine; copper dichloride / methanol / 18 h / 60 °C / 760.05 Torr / Cooling with liquid nitrogen View Scheme

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / 0 °C / Inert atmosphere 1.2: 1.5 h / 20 °C / Inert atmosphere 2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 5 h / Reflux; Inert atmosphere 3.1: dichloromethane / 0.08 h / 0 °C / Inert atmosphere 3.2: 12 h / 0 - 20 °C / Inert atmosphere 4.1: dichloro bis(acetonitrile) palladium(II); oxygen; triethylamine; copper dichloride / methanol / 18 h / 60 °C / 760.05 Torr / Cooling with liquid nitrogen View Scheme

1: 60 percent / tetrabutylammonium chloride / CH2Cl2; H2O / 12 h / Ambient temperature 2: 50 percent / acetonitrile / 12 h / Irradiation 3: 1.) cyclohexane, reflux, 15 h; 2.) 50 percent aq. acetic acid, reflux, 3 h View Scheme