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Issue 33, 2015
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The addition of bromine and iodine to palladacyclopentadienyl complexes bearing bidentate heteroditopic P−N spectator ligands derived from differently substituted quinolinic frames. The unexpected evolution of the reaction

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Abstract

We have synthesized two palladacyclopentadienyl derivatives bearing bidentate ligands heteroditopic 8-(diphenylphosphino)quinoline or 8-(diphenylphosphino)-2-methylquinoline. We have reacted the palladacyclopentadienyl complexes with Br2 and I2 to gain clues on the formation mechanism of the corresponding σ-butadienyl derivatives. We were able to obtain the pure σ-butadienyl derivative only in the case of Br2 reacting with the palladacyclopentadienyl complex bearing the unsubstituted quinoline. However, an equilibrium mixture of the σ-butadienyl and a novel zwitterionic species was obtained when the same complex reacts with I2. Furthermore, we have obtained exclusively an unprecedented zwitterionic complex when I2 reacts with the palladacyclopentadienyl complex bearing the substituted quinoline and a different ratio of an equilibrium mixture of σ-butadienyl and the zwitterionic species when the latter derivative reacts with Br2. The solid state structures of one σ-butadienyl complex and of the two novel zwitterionic derivatives were determined and an interpretation of the observed reactivity based on kinetic data and a computational study has been suggested.

Graphical abstract: The addition of bromine and iodine to palladacyclopentadienyl complexes bearing bidentate heteroditopic P−N spectator ligands derived from differently substituted quinolinic frames. The unexpected evolution of the reaction

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Publication details

The article was received on 19 May 2015, accepted on 19 Jul 2015 and first published on 20 Jul 2015


Article type: Paper
DOI: 10.1039/C5DT01884F
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Dalton Trans., 2015,44, 15049-15058

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    The addition of bromine and iodine to palladacyclopentadienyl complexes bearing bidentate heteroditopic P−N spectator ligands derived from differently substituted quinolinic frames. The unexpected evolution of the reaction

    L. Canovese, F. Visentin, T. Scattolin, C. Santo and V. Bertolasi, Dalton Trans., 2015, 44, 15049
    DOI: 10.1039/C5DT01884F

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