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  • Unexpected Intermediates and Products in the C−F Bond Activation of Tetrafluorobenzenes with a Bis(triethylphosphine)Nickel Synthon: Direct Evidence of a Rapid and Reversible C−H Bond Activation by Ni(0)
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  • The reaction of (PEt3)2Ni(η2-C14H10), a source of the reactive Ni(PEt3)2 moiety, with 1,2,4,5-F4C6H2 yields a mixture of three C−F bond activation products that include the unexpected products (PEt3)2NiF-2,3,5,6-F4C6H and (PEt3)2NiF-2,3,5-F3C6H2. Monitoring the reaction mixture via 19F and 1H NMR also reveals the presence of the C−H bond activation product, (PEt3)2NiH-2,3,5,6-F4C6H which is produced in a rapid equilibrium reaction. This observation provides insight into the steps necessary to modify nickel complexes for selective C−F bond activation in a variety of polyfluorinated aromatic substrates, but also expands the potential of simple nickel compounds for C−H bond activation and functionalization reactions.
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