Metal-Free Catalytic Hydrogenation of Enamines, Imines, and Conjugated Phosphinoalkenylboranes

Authors

  • Patrick Spies,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6503
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  • Sina Schwendemann,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6503
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  • Stefanie Lange,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6503
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  • Gerald Kehr Dr.,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6503
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  • Roland Fröhlich Dr.,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6503
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    • X-ray crystal structure analyses.

  • Gerhard Erker Prof. Dr.

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6503
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  • Financial support from the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie is gratefully acknowledged. We thank the BASF for a gift of solvents and Professor C. J. Elsevier for assistance with some of the NMR experiments.

Abstract

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The metal-free hydrogen activator 1 catalyzes the unique P/B hydrogenation of the frustrated Lewis pair 3, which itself is inactive toward H2 under the applied conditions, to yield the hydrogenation product 4. System 1/2 (5 mol %) also catalyzes the hydrogenation of a bulky ketimine and of enamines under mild conditions (2.5 bar H2, RT) to yield the respective amines.

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