Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation

A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic stud...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-12, Vol.80 (24), p.11993-11998
Main Authors: Seo, Hong-Ahn, Cho, Yeon-Ho, Lee, Ye-Sol, Cheon, Cheol-Hong
Format: Article
Language:English
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Summary:A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of α-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01922