2007
DOI: 10.1002/ejic.200600802
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Activation of Aromatic, Aliphatic, and Olefinic Carbon–Fluorine Bonds Using Cp*2HfH2

Abstract: The hafnium hydride Cp*2HfH2 is reacted with a series of fluorocarbons to examine the scope of C–F bond activation. Aromatic, vinylic, and aliphatic C–F bonds all show some degree of reactivity, and possible mechanisms are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Cited by 58 publications
(25 citation statements)
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“…[43,48,58] In contrast to aromatic or other unsaturated fluorocarbons containing π electrons, saturated PFCs have no strong binding site for interaction with a metal center. Radical pathways for the activation of these bonds by Zr and Hf hydrides have been successful, [114][115] as well as the recently reported conversion of aliphatic C-F bonds to C-H bonds using the R 3 Si + cation as a catalyst and R 3 SiH as the source of hydrogen atoms. [116][117] While the C-F bond is truly the strongest single bond to carbon, in part due to the polarity of the bond to electronegative fluorine, therein lies its Achilles' heel, as the electronegativity of fluorine also ensures that the C-F σ* antibonding orbitals are relatively low lying.…”
Section: Fluorocarbonsmentioning
confidence: 98%
“…[43,48,58] In contrast to aromatic or other unsaturated fluorocarbons containing π electrons, saturated PFCs have no strong binding site for interaction with a metal center. Radical pathways for the activation of these bonds by Zr and Hf hydrides have been successful, [114][115] as well as the recently reported conversion of aliphatic C-F bonds to C-H bonds using the R 3 Si + cation as a catalyst and R 3 SiH as the source of hydrogen atoms. [116][117] While the C-F bond is truly the strongest single bond to carbon, in part due to the polarity of the bond to electronegative fluorine, therein lies its Achilles' heel, as the electronegativity of fluorine also ensures that the C-F σ* antibonding orbitals are relatively low lying.…”
Section: Fluorocarbonsmentioning
confidence: 98%
“…Much of this recent activity is driven by the need for synthetic procedures to incorporate fluorine or a CF 3 group strategically in the synthesis of pharmaceuticals or PET reagents, leading to the development of new methodology for formation of C-F and C-CF 3 bonds [110][111][112][113][114][115][116][117][118][119][120][121][122]. Organometallic chemistry involving the chemical functionalization of C-F bonds also continues to be an active field [123][124][125][126][127][128][129][130][131][132][133][134][135][136].…”
Section: [ ( S C H E M E _ 4 ) T D $ F I G ]mentioning
confidence: 99%
“…Replacing zirconium by hafnium has no significant effect apart from reducing the reactivity,10f whereas moving to related titanium complexes weakens the metal–fluorine bond so that catalytic HDF becomes possible. Lentz et al.…”
Section: Fluorido Complex Formationmentioning
confidence: 99%