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Catalytic C-C Bond Formation Accomplished by Selective C-F Activation of Perfluorinated Arenes

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. C-C Coupling Reactions. X = I, Br and CH 3 SO 2. Kumada reaction Negishi reaction Stille reaction

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Catalytic C-C Bond Formation Accomplished by Selective C-F Activation of Perfluorinated Arenes

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  1. 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

  2. C-C Coupling Reactions X = I, Br and CH3SO2 • Kumada reaction • Negishi reaction • Stille reaction • Suzuki-Miyaura reaction • Heck reaction • Sonogashira reaction

  3. Transition-Metal-Mediated Conversions of aromatic C-F Bonds into C-C Bonds

  4. Transition-Metal-Mediated Conversions of Aromatic C-F Bonds into C-C Bonds

  5. Efficient C-F and C-C Activation by a Novel N-Heterocyclic Carbene-Nickel Complex

  6. Reaction of [Ni2(iPr2Im)4(COD)] with C7F8 and C12F10

  7. Structure Confirmed by 1H-NMR, 19F-NMR and X-ray Analysis

  8. The Catalytic Reaction of Per fluorotoluene with Phenyl Boronic Acid

  9. Suzuki Cross-Coupling Reactions of Perfluorinated Arenes

  10. Kumada-type Cross-Coupling reactions of polyfluorinated arenes

  11. 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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