Tetrahedron Letters p. 2907 - 2910 (1998)
Update date:2022-08-28
Topics:
Kubota, Hitoshi
Rice, Kenner C.
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.
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