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The direct alkynylation of tautomerizable heterocylcles is described via a two-step process involving in situ C-OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl(2)(CH(3)CN)(2) and 2-(dicyclohexylphosphino)biphenyl.

Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C−OH Bond Activation Using PyBrOP