Efficient Pd-catalyzed coupling of tautomerizable heterocycles with terminal alkynes via C-OH bond activation using PyBrOP.
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.
Shi
Ce
C
Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Aldrich
Courtney C
CC
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011810:Quinoxalines / Q000737:chemistry*; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
D000480:Alkynes; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; D011810:Quinoxalines; D014230:Triazoles; C496388:benzotriazol-1-yloxtri (pyrrolidinol)phosphonium hexafluorophosphate; D010165:Palladium
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