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Ruthenium-catalyzed Selective Monoamination of Vicinal Diols

Authors

  • Sebastian Bähn,

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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  • Annegret Tillack Dr.,

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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  • Sebastian Imm,

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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  • Kathleen Mevius,

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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  • Dirk Michalik Dr.,

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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  • Dirk Hollmann Dr.,

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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  • Lorenz Neubert,

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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  • Matthias Beller Prof.

    1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany), Fax: (+49) (381) 1281-51113
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Abstract

Highly selective monoamination of vicinal diols: The reaction of vicinal diols with primary and secondary amines is catalyzed by [Ru3(CO)12] and N-phenyl-2-(dicyclohexyl-phosphanyl)pyrrole to generate the corresponding amino alcohols with high selectivity and good yields.

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The monoamination of vicinal diols in the presence of in situ generated ruthenium catalysts has been investigated. Among the various phosphines tested in combination with [Ru3(CO)12], N-phenyl-2-(dicyclohexyl-phosphanyl)pyrrole showed the best performance. After optimization of the reaction conditions this system was applied to different secondary amines and anilines as well as a number of vicinal diols. With the exception of ethylene glycol, monoamination of the vicinal diols occurred selectively and the corresponding amino alcohols were obtained in good yields, producing water as the only side product.

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