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Aerobic Oxidative Conversion of Aromatic Aldehydes to Nitriles Using a Nitroxyl/NOx Catalyst System

Author:
Noh, Ji-Hyun, Kim, Jinho
Source:
Journal of organic chemistry 2015 v.80 no.22 pp. 11624-11628
ISSN:
1520-6904
Subject:
alcohols, aldehydes, catalysts, moieties, nitric acid, nitriles, nitrogen oxides, organic chemistry, oxidation, oxygen
Abstract:
The first transition-metal-free aerobic oxidative conversion of aldehyde catalyzed by a nitroxyl radical/NOₓ system is presented for the synthesis of nitrile. In the presence of a catalytic amount of 4-AcNH-TEMPO (4-acetamido-2,2,6,6-tetramethylpiperidine-N-oxyl), NaNO₂, and HNO₃, benzaldehydes bearing a variety of functional groups underwent condensation with NH₄OAc and following aerobic oxidation to produce nitriles selectively under an O₂ balloon. Aerobic oxidative conversion of a primary alcohol instead of aldehyde is also achieved by a one-pot sequential strategy.
Agid:
5504908