Polypyrrole-functionalized ruthenium carbene catalysts as efficient heterogeneous systems for olefin epoxidation

Mohamed Dakkach, Xavier Fontrodona, Teodor Parella, Ahmed Atlamsani, Isabel Romero, Montserrat Rodríguez

    Research output: Contribution to journalArticleResearchpeer-review

    9 Citations (Scopus)

    Abstract

    New Ru complexes containing the bpea-pyr ligand (bpea-pyr stands for N,N-bis(pyridin-2-ylmethyl)-3-(1H-pyrrol-1-yl)propan-1-amine), with the formula [RuCl2(bpea-pyr)(dmso)] (isomeric complexes 2a and 2b) or [Ru(CN-Me)(bpea-pyr)X)]n+ (CN-Me = 3-methyl-1-(pyridin-2-yl)-1H- imidazol-3-ium-2-ide; X = Cl, 3, or X = H2O, 4), have been prepared and fully characterized. Complexes 3 and 4 have been anchored onto an electrode surface through electropolymerization of the attached pyrrole group, yielding stable polypyrrole films. The electrochemical behaviour of 4, which displays a bielectronic Ru(IV/II) redox pair in solution, is dramatically affected by the electropolymerization process leading to the occurrence of two monoelectronic Ru(IV/III) and Ru(III/II) redox pairs in the heterogeneous system. A carbon felt modified electrode containing complex 4 (C-felt/poly-4) has been evaluated as a heterogeneous catalyst in the epoxidation of various olefin substrates using PhI(OAc)2 as an oxidant, displaying TON values of several thousands in all cases and good selectivity for the epoxide product. © 2014 The Royal Society of Chemistry.
    Original languageEnglish
    Pages (from-to)9916-9923
    JournalDalton Transactions
    Volume43
    Issue number26
    DOIs
    Publication statusPublished - 14 Jul 2014

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