The Journal of Organic Chemistry · 2001 · 56 citations · 3 references
Natural SciencesChemistryCatalysisInorganic ChemistryOrganic ChemistryHeterocyclic ChemistryHeterocyclic CompoundsAlkyne Cycloaddition ReactionsHeterocyclic ReactivityNickel-catalyzed Cross-couplingRegioselectivitySubstituent Effects On Cyclooctyne ReactivitySubstituent Selectivity EffectsTransition-metal-catalyzed Heterocycle Synthesis
We report the highly regioselective cyclotrimerization of the 1-perfluoroalkylenynes in the presence of Ni(PPh3)4. The substituent effects on the reactivity of the enynes were investigated. We also succeeded in the nickel-catalyzed cocyclization of the 1-perfluoroalkylenynes with (trimethylsilyl)-acetylene. The possible structures of the intermediates of the cyclotrimerization and the reasons for the observed high regioselectivity were discussed.
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L. S. Meriwether, E. C. COLTHUP, G. W. Kennerly · The Journal of Organic Chemistry · 1961 · 45 citations