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Synthesis 2009(8): 1370-1374
DOI: 10.1055/s-0028-1087994
DOI: 10.1055/s-0028-1087994
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkIBX/TBAB-Mediated Oxidation of Primary Amines to Nitriles
Further Information
Received
2 November 2008
Publication Date:
06 March 2009 (online)
Publication History
Publication Date:
06 March 2009 (online)

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