Mechanistic analysis proposes a palladium(II)/palladium(IV) catalytic pathway for Heck olefination reactions, suggesting alternative routes involving reversible nucleophilic addition.
A mechanism for the olefination reaction is proposed, involving PdII/PdIV, in which a key step is reversible nucleophilic attack on the PdII-coordinated olefin to give an electron-rich σ-alkyl- or, with carbonate, a chelated σ-dialkyl-complex, which then oxidatively adds the organic halide e.g. ArX. Loss of nucleophile, migration of Ar from PdIV to coordinated olefin, β-hydrogen elimination and loss of HX then gives the product of olefination and regenerates the PdII catalyst.
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Bernard L. Shaw (1998) studied this question.
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