1. 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

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
Base
NEt3
K2CO3 KF
NaOH/KF
Yield (%) 83 54 59 44

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.