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

  1. Dr. Christian Fischer1,
  2. Dr. Stefan Schulz1,
  3. Dr. Hans-Joachim Drexler1,
  4. Carmen Selle1,
  5. Dr. Matthias Lotz2,
  6. Dr. Mathias Sawall3,
  7. Prof. Dr. Klaus Neymeyr3,
  8. Prof. Dr. Detlef Heller1,*

Article first published online: 17 NOV 2011

DOI: 10.1002/cctc.201100277

Issue

ChemCatChem

ChemCatChem

Volume 4, Issue 1, pages 81–88, January 2, 2012

Additional Information

How to Cite

Fischer, C., Schulz, S., Drexler, H.-J., Selle, C., Lotz, M., Sawall, M., Neymeyr, K. and Heller, D. (2012), The Influence of Substituents in Diphosphine Ligands on the Hydrogenation Activity and Selectivity of the Corresponding Rhodium Complexes as Exemplified by ButiPhane. ChemCatChem, 4: 81–88. doi: 10.1002/cctc.201100277

Author Information

  1. 1

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

  2. 2

    Solvias AG, Klybeckstr. 191, Postfach, CH-4002 Basel (Switzerland)

  3. 3

    Universität Rostock, Institut für Mathematik, Ulmenstr. 69, 18057 Rostock (Germany)

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

Publication History

  1. Issue published online: 27 DEC 2011
  2. Article first published online: 17 NOV 2011
  3. Manuscript Received: 15 AUG 2011

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Keywords:

  • asymmetric hydrogenation;
  • ButiPhane;
  • homogeneous catalysis;
  • rhodium;
  • UV/Vis spectroscopy

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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