1: 1,3-dimethoxy benzene With n-butyllithium in tetrahydrofuran; hexane T=0 - 25°C; 5 h; Inert atmosphere; 2: 4,5-dibromoveratrole in tetrahydrofuran; hexane T=-35 - 25°C; Inert atmosphere;

1: lithium diisopropyl amide / tetrahydrofuran / 1.25 h / -78 °C 2: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 3: iodine cloride / dichloromethane / 48 h / -78 - 20 °C / |Inert atmosphere 4: tetrabutylammomium bromide; sodium dithionite; potassium hydroxide / tetrahydrofuran; water / 40 °C / |Inert atmosphere 5: bis(1,5-cyclooctadiene)nickel (0); cyclooctadiene; [2,2']bipyridinyl / N,N-dimethyl-formamide; toluene / 2 h / 65 - 85 °C / |Schlenk technique; |Darkness View Scheme

ammonia in N-methyl-acetamide

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium(0); polymethylhydroxysilane in N,N-dimethyl acetamide T=120°C; 2.5 h;

1: n-butyllithium / tetrahydrofuran; hexane; toluene / -50 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 2 h / 20 °C / Inert atmosphere 3: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 48 h / 20 °C / Inert atmosphere 4: sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 0.07 h / 0 °C 5: dimethyl sulfoxide / Irradiation; Cooling; Inert atmosphere View Scheme

n-butyllithium in tetrahydrofuran; hexane T=-78°C; 5 h;