Ligand effects in rhodium-catalyzed hydroformylation with bisphosphines: steric or electronic?

Yunzhe Jiao (Corresponding author), Marta Serrano Torne, Jose Gracia, J.W. Niemantsverdriet, Piet W.N.M. van Leeuwen (Corresponding author)

    Research output: Contribution to journalArticleAcademicpeer-review

    19 Citations (Scopus)

    Abstract

    Twelve commercially available bisphosphine ligands have been evaluated in rhodium-catalyzed hydroformylation reactions. All ligands exhibited high chemoselectivities for aldehyde formation. The highest enantioselectivity (53% ee) of styrene hydroformylation was achieved with (S)-BTFM-Garphos (L7) substituted with electron withdrawing substituents. High pressure NMR (HP-NMR) spectroscopy and in situ high pressure IR spectroscopy (HP-IR) were used to study the resting states of the catalyst species in the reactions. The ligand effect on the structures of the observable species was examined. Both electronic and steric factors were considered to contribute to the performance of the various ligands. The results showed that decreasing the phosphine basicity increased the enantioselectivity, while in the systems studied here the steric character plays a less important role than the electronic features in achieving good regioselectivities.

    Original languageEnglish
    Pages (from-to)1404-1414
    Number of pages11
    JournalCatalysis Science and Technology
    Volume7
    Issue number6
    DOIs
    Publication statusPublished - 21 Mar 2017

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