Dehydrogenative Oxidation of Primary Amines to Nitriles

Kuei-Nin T. Tseng; Nathaniel K. Szymczak

doi:10.1055/s-0034-1378543

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(17): 2385-2389
DOI: 10.1055/s-0034-1378543

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Dehydrogenative Oxidation of Primary Amines to Nitriles

Kuei-Nin T. Tseng

Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA Fax: +1(734)6474865 eMail: nszym@umich.edu

,

Nathaniel K. Szymczak*

Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA Fax: +1(734)6474865 eMail: nszym@umich.edu

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Abstract

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Abstract

Homogeneous catalysts can promote the oxidation of primary amines to nitriles without added chemical oxidants. An amide-derived N,N,N-ruthenium(II)–hydride complex was discovered that promotes the dehydrogenation of primary and secondary amines to the corresponding nitriles and imines with concomitant liberation of H₂, notably without added hydrogen acceptor or base. The dehydrogenative protocol is tolerant of substrates that contain oxidizable functionality and is selective for the dehydrogenation of primary amines (-CH₂NH₂) in the presence of amines without α-CH hydrogens.

Key words

homogeneous catalysis - amines - dehydrogenation - nitriles - chemoselectivity

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References and Notes

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