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46.5.1.3.2 Variation 2: Nickel-Mediated C—H Activation

DOI: 10.1055/sos-SD-046-00090

Gandon, V.; Thorimbert, S.; Malacria, M.Science of Synthesis, (200946182.

Linear 2:1 co-oligomerization between an acrylate and an alkyne can be achieved using certain nickel complexes but, as for cobalt, it is difficult to predict whether a cyclic or a linear compound will be isolated at the end of the process. Nevertheless, 1,3,5-trienes are obtained from interactions between alkenes, alkynes, and nickel complexes [NiX2(PPh3)2 (X=Cl, Br, I)] in contact with zinc dust; for example, the triene 33 is available when 2.8 molecular equivalents of ethyl acrylate are combined with a single equivalent of 1-phenylprop-1-yne using diiodobis(triphenylphosphine)nickel(II) as the catalyst (Scheme 12)[‌20‌].

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