Catalytic C-F bond activation of geminal difluorocyclopropanes by nickel(I) complexes via a radical mechanism

Nickel(II)fluorido complexes bearing NNN-pincer ligands were found to be catalysts in the hydrodefluorination of geminal difluorocyclo-propanes which undergo ring-opening to form the corresponding monofluoroalkenes in good yield and high Z-selectivities. Evidence for a radical based mechanism involv...

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Published inChemical communications (Cambridge, England) Vol. 52; no. 1; pp. 202 - 205
Main Authors Wenz, Jan, Rettenmeier, Christoph A., Wadepohl, Hubert, Gade, Lutz H.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
FLUORINATED BUILDING-BLOCKS
ORGANIC-SYNTHESIS
FLUOROARENES
GEM-DIFLUORINATED CYCLOPROPANES
EFFICIENT APPROACH
MACROCYCLE
CHEMISTRY
DIFLUOROCARBENE SOURCE
METAL-COMPLEXES
HYDRODEFLUORINATION
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Summary:Nickel(II)fluorido complexes bearing NNN-pincer ligands were found to be catalysts in the hydrodefluorination of geminal difluorocyclo-propanes which undergo ring-opening to form the corresponding monofluoroalkenes in good yield and high Z-selectivities. Evidence for a radical based mechanism involving nickel(I) and nickel hydrido complexes as key intermediates was obtained in the corresponding stoichiometric reactions.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc08950f