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Issue 1, 2012
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Electrochemical nickel-induced fluoroalkylation: synthetic, structural and mechanistic study

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Abstract

Electrocatalytic generation of nickel catalysts in low oxidation states by reduction of nickel complexes with various ligands (2,2′-bipyridine, 2,2′:6′,2′′-terpyridine, (S,S)-2,6-bis(4-phenyl-2-oxazolin-2-yl)-pyridine) in the presence of olefinic substrates and fluoroalkyl halides leads to new organic products derived from addition-dimerization processes. Due to the presence of two stereocenters in the dimerization products two diastereomers were characterized by a variety of analytical techniques including multi-dimensional NMR methods and X-ray single crystal diffraction. The formation of dimers was prevented by the inclusion of the hydrogen atom donor tributyltin hydride. The cyclic voltammetry study of selected nickel complexes along with fluoroalkyl halides demonstrated that Ni(I)L is the active form of the catalyst.

Graphical abstract: Electrochemical nickel-induced fluoroalkylation: synthetic, structural and mechanistic study

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Publication details

The article was received on 07 Jul 2011, accepted on 04 Oct 2011 and first published on 15 Nov 2011


Article type: Paper
DOI: 10.1039/C1DT11299F
Citation: Dalton Trans., 2012,41, 165-172
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    Electrochemical nickel-induced fluoroalkylation: synthetic, structural and mechanistic study

    D. Mikhaylov, T. Gryaznova, Y. Dudkina, M. Khrizanphorov, S. Latypov, O. Kataeva, D. A. Vicic, O. G. Sinyashin and Y. Budnikova, Dalton Trans., 2012, 41, 165
    DOI: 10.1039/C1DT11299F

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