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Asymmetric Homogeneous Hydrogenation in Flow using a Tube-in-Tube Reactor

Authors

  • Sean Newton,

    Corresponding author
    1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K. Fax: (+44)-01223-336-442; phone: (+44)-01223-336-698
    • Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K. Fax: (+44)-01223-336-442; phone: (+44)-01223-336-698
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  • Steven V. Ley,

    Corresponding author
    1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K. Fax: (+44)-01223-336-442; phone: (+44)-01223-336-698
    • Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K. Fax: (+44)-01223-336-442; phone: (+44)-01223-336-698
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  • Eva Casas Arcé,

    1. Johnson–Matthey Catalysis and Chiral Technology, Cambridge Science Park, Unit 28, Cambridge, CB4 0FP, U.K.
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  • Damian M. Grainger

    1. Johnson–Matthey Catalysis and Chiral Technology, Cambridge Science Park, Unit 28, Cambridge, CB4 0FP, U.K.
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Abstract

In this update, the asymmetric homogeneous hydrogenation of a number of trisubstituted olefins utilizing the recently developed tube-in-tube gas-liquid flow reactor is described. A number of chiral iridium- and rhodium-based catalysts and other parameters such as pressure, solvent, temperature and catalyst loading were screened. The advantage of the flow set-up for rapid screening and optimization of reaction parameters is illustrated. Furthermore, a comparative study using batch conditions aided in the optimization of the flow reaction set-up. The set-up was further modified to recycle the catalyst which prolonged catalytic activity.

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