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Thomas Schaub, Marc Backes, and Udo Radius*
Catalytic C-C Bond Formation Accomplished by Selective C-F Activation of Perfluorinated Arenes Thomas Schaub, Marc Backes, and Udo Radius* J. Am. Chem. Soc. 2006, 128, 15964
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C-C Coupling Reactions
X = I, Br and CH3SO2 Kumada reaction Negishi reaction Stille reaction Suzuki-Miyaura reaction Heck reaction Sonogashira reaction
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Transition-Metal-Mediated Conversions of aromatic C-F Bonds into C-C Bonds
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Transition-Metal-Mediated Conversions of Aromatic C-F Bonds into C-C Bonds
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Efficient C-F and C-C Activation by a Novel N-Heterocyclic Carbene-Nickel Complex
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Reaction of [Ni2(iPr2Im)4(COD)] with C7F8 and C12F10
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Structure Confirmed by 1H-NMR, 19F-NMR and X-ray Analysis
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The Catalytic Reaction of Per fluorotoluene with Phenyl Boronic Acid
Base NEt3 K2CO3 KF NaOH/KF Yield (%) 83 54 59 44
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Suzuki Cross-Coupling Reactions of Perfluorinated Arenes
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Kumada-type Cross-Coupling reactions of polyfluorinated arenes
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Conclusions We report here the first example of a catalytically active system for Suzuki-type cross-coupling reactions of perfluorinated arenes such as octafluorotoluene and perfluorobiphenyl, which combines C-F activation of these substrates efficiently with C-C coupling reactions. Work to expand the scope of this metal-catalyzed cross-coupling reaction of aryl fluorides and applying this concept to other transformations is currently in progress.
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