An easy synthetic route from substituted catechols via their corresponding aryl bistriflates to substituted phthalonitriles is described. The displacement of the triflate groups in catechol triflates by cyanide ions proceeded in high yields using zinc cyanide and palladium-1,1′-bis(diphenylphosphino)ferrocene as catalyst. The mild reaction conditions tolerate numerous functional groups and represent a desirable alternative to the generally low-yielding Rosenmund-von Braun reaction.
Iodide acceleration in the Pd-catalyzed coupling of aromatic 1,2-ditriflates with alkynes: Synthesis of enediynes
Aryl enediyenes have been synthesized in a one-pot procedure by a Pd-catalyzed coupling of terminal alkynes and ortho-aryl ditriflates. A variety of substrates have been examined.
Powell, Noel A.,Rychnovsky, Scott D.
p. 7901 - 7904
(2007/10/03)
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