Catalytic Carbon−Carbon and Carbon−Silicon Bond Activation and Functionalization by Nickel Complexes

The nickel alkyne complexes (dippe)Ni(Me3SiC⋮CSiMe3), 1, (dippe)Ni(Me3CC⋮CSiMe3), 2, and (dippe)Ni(MeC⋮CSiMe3), 3, were synthesized (dippe = bis(diisopropylphosphino)ethane) and characterized by 1H, 31P, and 13C{1H} NMR spectroscopy. Complex 1 was characterized by X-ray crystallography. Heating comp...

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Bibliographic Details
Published in:Organometallics 1999-10, Vol.18 (22), p.4660-4668
Main Authors: Edelbach, Brian L, Lachicotte, Rene J, Jones, William D
Format: Article
Language:English
Subjects:
40 CHEMISTRY
ALKYNES
CHEMICAL ACTIVATION
CHEMICAL REACTION KINETICS
CRYSTAL STRUCTURE
HOMOGENEOUS CATALYSIS
NICKEL COMPLEXES
SILANES
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Summary:The nickel alkyne complexes (dippe)Ni(Me3SiC⋮CSiMe3), 1, (dippe)Ni(Me3CC⋮CSiMe3), 2, and (dippe)Ni(MeC⋮CSiMe3), 3, were synthesized (dippe = bis(diisopropylphosphino)ethane) and characterized by 1H, 31P, and 13C{1H} NMR spectroscopy. Complex 1 was characterized by X-ray crystallography. Heating complex 1, 2, or 3 with excess biphenylene and alkyne results in the catalytic formation of several novel organic compounds, several of which have been characterized by X-ray crystallography. These reactions are proposed to proceed by a competition between β-silyl migration from an acetylene insertion intermediate and elimination of phenanthrene. Mechanistic schemes are presented for these reactions.
ISSN:0276-7333
1520-6041
DOI:10.1021/om990457l