magnesium in tetrahydrofuran T=30 - 50°C; 4 h; Inert atmosphereSonication;

in diethyl ether; n-heptane T=0 - 20°C; Inert atmosphere;

1: hydrogenchloride / n-heptane; water / 0.5 h / 20 °C 2: iodine; magnesium / tetrahydrofuran / 4 h / |Inert atmosphere; |Sonication View Scheme

1: iodine / methanol / 60 °C / |Reflux 2: hydrogenchloride / n-heptane; water / 0.5 h / 20 °C View Scheme

tetrakis(triphenylphosphine) palladium(0) in toluene Stille Cross Coupling; Reflux;

1: iodine / methanol / 60 °C / |Reflux 2: hydrogenchloride / n-heptane; water / 0.5 h / 20 °C 3: sodium azide / water / 5 h / 20 °C / |Cooling View Scheme

in tetrahydrofuran byproducts: phenylboronic acid; to srirred soln. of Sn-compound in THF was added soln. of BH3 in THF under N2, mixt. was left at room temp. for 1 h, refluxed for 1 h, cooled, Et2O and water was added; dried with MgSO4, solvent was removed under vac., column chromy. on silica gel with hexane and hexane-Et2O, recrystd. from water;

1: iodine / methanol / 60 °C / |Reflux 2: hydrogenchloride / n-heptane; water / 0.5 h / 20 °C 3: sodium tetrahydroborate / propan-1-ol / 20 °C View Scheme

1: tri-n-octyl(phenyl)stannane With iodine in methanol T=65°C; 2: potassium acetate in methanol 5 h; Heating;