Formamidines – Versatile Ligands for Zinc-Catalyzed Hydrosilylation and Iron-Catalyzed Epoxidation Reactions

Authors

  • Stephan Enthaler,

    1. Technische Universität Berlin, Department of Chemistry,Cluster of Excellence “Unifying Concepts in Catalysis”, Straße des 17. Juni 135, 10623 Berlin, Germany, Fax: +49-3031429732
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  • Kristin Schröder,

    1. Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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  • Shigeyoshi Inoue,

    1. Technische Universität Berlin, Department of Chemistry,Cluster of Excellence “Unifying Concepts in Catalysis”, Straße des 17. Juni 135, 10623 Berlin, Germany, Fax: +49-3031429732
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  • Björn Eckhardt,

    1. Technische Universität Berlin, Department of Chemistry,Cluster of Excellence “Unifying Concepts in Catalysis”, Straße des 17. Juni 135, 10623 Berlin, Germany, Fax: +49-3031429732
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  • Kathrin Junge,

    1. Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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  • Matthias Beller,

    1. Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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  • Matthias Drieß

    1. Technische Universität Berlin, Department of Chemistry,Cluster of Excellence “Unifying Concepts in Catalysis”, Straße des 17. Juni 135, 10623 Berlin, Germany, Fax: +49-3031429732
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Abstract

In the present study the abilities of catalysts modified by formamidine ligands have been examined in the zinc-catalyzed hydrosilylation of ketones and the iron-catalyzed epoxidation of stilbene. In case of hydrosilylation diethylzinc combined with easily accessible formamidine ligands allow for the efficient reduction of various aryl and alkyl ketones. By using a convenient in situ catalyst system high turnover frequencies up to more than 1.000 h–1 and a broad functional group tolerance were achieved. Moreover, the formamidine ligands were successfully applied in the iron-catalyzed epoxidation of stilbene with hydrogen peroxide in good yield and chemoselectivity.

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