Journal
ORGANOMETALLICS
Volume 32, Issue 17, Pages 4785-4792Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om400492g
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Funding
- RFBR [11-03-92662-MCXa]
- Russian Ministry of Science and Education [8446]
- U.S. NSF [CHE-1124619]
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The electochemical oxidation of palladium acetate or palladium perfluoroacetate in the presence of 2-phenylpyridine promotes catalytic ortho C-H substitution reactions. As possible intermediates, Pd(II) metallacycles with Pd-bound acetate, perfluoroacetate, and perfluoroheptanoate substituents have been isolated and characterized: binuclear [(PhPy)Pd(mu-OAc)](2) and [(PhPy) Pd(mu-TFA)](2) and mononuclear [(PhPy)Pd(TFA)](CH3CN), [(PhPy)Pd(TFA)](PhPy), and [(PhPy)Pd(PFH)](PhPy). The fluorinated derivatives were found to exist in solvent-dependent equilibria between mononuclear and binuclear forms. Cyclic voltammetry was used to elucidate redox properties of the palladacycles and the oxidation route to the final products.
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