Homogeneous cobalt-catalyzed reductive amination for synthesis of functionalized primary amines

Kathiravan Murugesan, Zhihong Wei, Vishwas G. Chandrashekhar, Helfried Neumann, Anke Spannenberg, Haijun Jiao, Matthias Beller () and Rajenahally V. Jagadeesh ()
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Kathiravan Murugesan: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Zhihong Wei: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Vishwas G. Chandrashekhar: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Helfried Neumann: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Anke Spannenberg: Leibniz-Institut für Katalyse e.V. an der Universität Rostock
Haijun Jiao: 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, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract The development of earth abundant 3d metal-based catalysts continues to be an important goal of chemical research. In particular, the design of base metal complexes for reductive amination to produce primary amines remains as challenging. Here, we report the combination of cobalt and linear-triphos (bis(2-diphenylphosphinoethyl)phenylphosphine) as the molecularly-defined non-noble metal catalyst for the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds, gaseous ammonia and hydrogen in good to excellent yields. Noteworthy, this cobalt catalyst exhibits high selectivity and as a result the -NH2 moiety is introduced in functionalized and structurally diverse molecules. An inner-sphere mechanism on the basis of the mono-cationic [triphos-CoH]+ complex as active catalyst is proposed and supported with density functional theory computation on the doublet state potential free energy surface and H2 metathesis is found as the rate-determining step.

Date: 2019
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DOI: 10.1038/s41467-019-13351-7

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