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Synthesis 2009(8): 1370-1374  
DOI: 10.1055/s-0028-1087994
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

IBX/TBAB-Mediated Oxidation of Primary Amines to Nitriles

Fleur Drouet, Patrice Fontaine, Géraldine Masson*, Jieping Zhu*
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: zhu@icsn.cnrs-gif.fr; e-Mail: masson@icsn.cnrs-gif.fr;
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Publikationsverlauf

Received 2 November 2008
Publikationsdatum:
06. März 2009 (online)

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Abstract

The combination of o-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) efficiently oxidizes primary amines to the corresponding nitriles in good to excellent yield under mild conditions. The reaction is racemization-free when applied to a chiral lysine derivative.

Key words

o-iodoxybenzoic acid (IBX) - tetrabutylammonium bromide (TBAB) - amines - nitriles - oxidation - dehydrogenation

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27

We thank one of the referees for pointing out this mechanistic consideration and related references.