Palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide

Article abstract of DOI:10.1016/S0040-4039(98)00414-6

We examined the palladium-catalyzed cyanation of hindered, electron- rich aryl triflates by zinc cyanide using 2-methoxyphenyl trifluoromethanesulfonate (4 as a model compound. The reaction with two equivalents of Zn(CN)₂ and catalytic Pd(PPh₃)₄ in DMF at 120°C for 2 hr afforded 2-methoxybenzonitrile (5) in 81% yield. The synthesis of 3-cyano-3- desoxynaltrexone (3), which had not previouly been obtained by the reaction with potassium or sodium cyanide as a cyanide source, was achieved by applying this procedure to its corresponding triflate 2.