The Influence of Substituents in Diphosphine Ligands on the Hydrogenation Activity and Selectivity of the Corresponding Rhodium Complexes as Exemplified by ButiPhane

Authors

  • Dr. Christian Fischer,

    1. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000
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  • Dr. Stefan Schulz,

    1. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000
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  • Dr. Hans-Joachim Drexler,

    1. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000
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  • Carmen Selle,

    1. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000
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  • Dr. Matthias Lotz,

    1. Solvias AG, Klybeckstr. 191, Postfach, CH-4002 Basel (Switzerland)
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  • Dr. Mathias Sawall,

    1. Universität Rostock, Institut für Mathematik, Ulmenstr. 69, 18057 Rostock (Germany)
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  • Prof. Dr. Klaus Neymeyr,

    1. Universität Rostock, Institut für Mathematik, Ulmenstr. 69, 18057 Rostock (Germany)
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  • Prof. Dr. Detlef Heller

    Corresponding author
    1. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000
    • Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29 A, 18059 Rostock (Germany), Fax: (+49) 381-12815000
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Abstract

The influence of substituents in ButiPhane ligands (with R=Me, Et, iPr) on the hydrogenation activity and selectivity of the corresponding rhodium complexes has been quantitatively assessed. Increasingly demanding substituents negatively affect the reduction rate of 1,5-cyclooctadiene in catalyst precursors en route to catalytically active MeOH–solvent complexes. The same trend as to activity is observed in the hydrogenation of prochiral olefins [methyl-(Z)-α-acetamidocinnamate, methyl (Z)-3-N-acetylamino-3-methylacrylate, and methyl (Z)-3-N-acetylamino-3-phenylacrylate], which however is counterbalanced by an increase in the stereorecognition ability of the bulkier catalysts.

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