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

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

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33 Citations (Scopus)


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
Issue number24
Publication statusPublished - 2015 Nov 18

Bibliographical note

Funding Information:
This work was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean Government (NRF-2013R1A1A1008434 and NRF-20100020209). We are also thankful for an NRF grant (NRF-2014-011165, Center for New Directions in Organic Synthesis).

Publisher Copyright:
© 2015 American Chemical Society.

ASJC Scopus subject areas

  • Organic Chemistry


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