IBX/TBAB-mediated oxidation of primary amines to nitriles

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 deriv. [on SciFinder (R)]


Published in:
Synthesis, 8, 1370-1374
Year:
2009
Keywords:
Note:
CAN 151:147834
23-19
Aliphatic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0039-7881
written in English.
64-04-0 (2-Phenylethylamine); 89-97-4 (2-Chlorobenzylamine); 111-68-2 (1-Aminoheptane); 120-20-7; 124-09-4 (1,6-Diaminohexane); 2393-23-9 (4-Methoxybenzylamine); 2620-50-0 (3,4-Methylenedioxybenzylamine); 13214-66-9 (4-Phenylbutylamine); 75178-96-0; 188625-18-5; 1171183-38-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of nitriles via IBX-TBAb-mediated oxidn. of primary amines); 1643-19-2 (Tetrabutylammonium bromide); 61717-82-6 Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of nitriles via IBX-TBAb-mediated oxidn. of primary amines); 93-17-4P (2-(3,4-Dimethoxyphenyl)acetonitrile); 111-69-3P (Adiponitrile); 140-29-4P (Phenylacetonitrile); 629-08-3P (Heptanenitrile); 873-32-5P (2-Chlorobenzonitrile); 874-90-8P (4-Methoxybenzonitrile); 2046-18-6P (4-Phenylbutyronitrile); 4421-09-4P (3,4-Methylenedioxybenzonitrile); 53588-95-7P; 295778-53-9P; 1171183-40-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of nitriles via IBX-TBAb-mediated oxidn. of primary amines)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


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