Selectivity in the aliphatic palladation of ketone hydrazones. An example of palladium-promoted intramolecular addition of a N,N-dimethylhydrazone to an alkene

Article abstract of DOI:10.1021/om00009a056

The efficacy of the aliphatic palladation reaction diminishes with the nucleophilicity of the hydrazone imino nitrogen; no benzylic or allylic C-H activation was observed. A γ,δ-unsaturated dimethyl-hydrazone reacts with Pd(PPh₃)₂Cl₂ to yield a palladacycle resulting from the addition of the imino group to a (η²-alkene)palladium complex.