IBX/TBAB-mediated oxidation of primary amines to nitriles
2009
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 deriv. [on SciFinder (R)]
Details
Title
IBX/TBAB-mediated oxidation of primary amines to nitriles
Author(s)
Drouet, Fleur ; Fontaine, Patrice ; Masson, Geraldine ; Zhu, Jieping
Published in
Synthesis
Issue
8
Pages
1370-1374
Date
2009
ISSN
0039-7881
Keywords
Oxidation (prepn. of nitriles via IBX-TBAb-mediated oxidn. of primary amines); Nitriles Role: SPN (Synthetic preparation); PREP (Preparation) (prepn. of nitriles via IBX-TBAb-mediated oxidn. of primary amines); Amines Role: RCT (Reactant); RACT (Reactant or reagent) (primary; prepn. of nitriles via IBX-TBAb-mediated oxidn. of primary amines); nitrile prepn; primary amine oxidn IBX TBAB
Note
CAN 151:147834
23-19
Aliphatic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
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)
23-19
Aliphatic Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
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
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25