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

Hong Ahn Seo, Yeon Ho Cho, Ye Sol Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)11993-11998
Number of pages6
JournalJournal of Organic Chemistry
Volume80
Issue number24
DOIs
Publication statusPublished - 2015 Nov 18

Fingerprint

Imines
Cyanides
Amides
Metals
Oxidation
Nitriles
Proton transfer
Molecular oxygen
Aldehydes
Protons
Nitrogen
Carbon
Air
Oxygen

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation. / Seo, Hong Ahn; Cho, Yeon Ho; Lee, Ye Sol; Cheon, Cheol-Hong.

In: Journal of Organic Chemistry, Vol. 80, No. 24, 18.11.2015, p. 11993-11998.

Research output: Contribution to journalArticle

Seo, Hong Ahn ; Cho, Yeon Ho ; Lee, Ye Sol ; Cheon, Cheol-Hong. / Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 24. pp. 11993-11998.
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