iodine in tetrahydrofuran; toluene 24 h; Photolysis;

1: With hydrogenchloride; sodium nitrite T=-5°C; Diazotization; 0.25 h; 2: With HPF6 in water T=5°C; Substitution; 2 h; 3: in xylene Decomposition; Heating;

1: methylethyl sulfide; palladium diacetate; silver carbonate; 2,2,2-trimethylacetic acid / 8 h / 120 °C / Inert atmosphere 2: [bis(acetoxy)iodo]benzene / 1,4-dioxane / 8 h / 20 °C / Air atmosphere; Irradiation View Scheme

1: palladium diacetate; 1-(phenyl(piperidin-1-yl)methyl)naphthalene-2-ol; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl acetamide / 40 h / 140 °C / |Inert atmosphere 2: iodine / tetrahydrofuran; toluene / 24 h / |Photolysis View Scheme

(i) MeMgI, (ii) CoCl2; Multistep reaction;