Synlett 2014; 25(17): 2385-2389
DOI: 10.1055/s-0034-1378543
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 03 June 2014

Accepted after revision: 02 July 2014

Publication Date:
21 August 2014 (online)

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.

 
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