Simple ruthenium-catalyzed reductive amination enables the synthesis of a broad range of primary amines

Thirusangumurugan Senthamarai, Kathiravan Murugesan, Jacob Schneidewind, Narayana V. Kalevaru, Wolfgang Baumann, Helfried Neumann, Paul C. J. Kamer, Matthias Beller () and Rajenahally V. Jagadeesh ()
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Thirusangumurugan Senthamarai: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Kathiravan Murugesan: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Jacob Schneidewind: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Narayana V. Kalevaru: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Wolfgang Baumann: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Helfried Neumann: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Paul C. J. Kamer: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Matthias Beller: Leibniz-Institut für Katalyse e. V. an der Universität Rostock
Rajenahally V. Jagadeesh: Leibniz-Institut für Katalyse e. V. an der Universität Rostock

Nature Communications, 2018, vol. 9, issue 1, 1-12

Abstract: Abstract The production of primary benzylic and aliphatic amines, which represent essential feedstocks and key intermediates for valuable chemicals, life science molecules and materials, is of central importance. Here, we report the synthesis of this class of amines starting from carbonyl compounds and ammonia by Ru-catalyzed reductive amination using H2. Key to success for this synthesis is the use of a simple RuCl2(PPh3)3 catalyst that empowers the synthesis of >90 various linear and branched benzylic, heterocyclic, and aliphatic amines under industrially viable and scalable conditions. Applying this catalyst, −NH2 moiety has been introduced in functionalized and structurally diverse compounds, steroid derivatives and pharmaceuticals. Noteworthy, the synthetic utility of this Ru-catalyzed amination protocol has been demonstrated by upscaling the reactions up to 10 gram-scale syntheses. Furthermore, in situ NMR studies were performed for the identification of active catalytic species. Based on these studies a mechanism for Ru-catalyzed reductive amination is proposed.

Date: 2018
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DOI: 10.1038/s41467-018-06416-6

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