The Journal of Organic Chemistry · 2005 · 226 citations · 15 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCatalyst DesignCatalyst PreparationCatalyst SynthesisCross-coupling ReactionsHeterocycle SynthesisSolvent-free SynthesisAryl Halide CouplingCopper-catalyzed CouplingCross-coupling CatalysisPalladium CatalystsPalladium-catalyzed Cross-couplingSolvent-free CatalysisSolvent-free Cycloaddition ReactionsSonogashira Coupling
[reaction: see text] PdCl2(PPh3)2 combined with TBAF under solvent-free conditions provided general and fast Sonogashira cross-coupling reactions of aryl halides with terminal alkynes. In particular, this protocol could be applied to the reactions of deactivated aryl chlorides. In the presence of 3 mol % of PdCl2(PPh3)2 and 3 equiv of TBAF, a number of ArX species (X = I, Br, Cl) were coupled with alkynes to afford the corresponding products in moderate to excellent yields under copper-, amine-, and solvent-free conditions.
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B. M. Choudary, Sateesh Madhi, Naidu S. Chowdari et al. · Journal of the American Chemical Society · 2002 · 697 citations