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Issue 6, 2017
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Ligand effects in rhodium-catalyzed hydroformylation with bisphosphines: steric or electronic?

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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.

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

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Publication details

The article was received on 19 Sep 2016, accepted on 07 Feb 2017 and first published on 08 Feb 2017


Article type: Paper
DOI: 10.1039/C6CY01990K
Citation: Catal. Sci. Technol., 2017,7, 1404-1414
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    Ligand effects in rhodium-catalyzed hydroformylation with bisphosphines: steric or electronic?

    Y. Jiao, M. S. Torne, J. Gracia, J. W. (. Niemantsverdriet and P. W. N. M. van Leeuwen, Catal. Sci. Technol., 2017, 7, 1404
    DOI: 10.1039/C6CY01990K

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