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

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

doi:10.1021/acs.joc.5b01922

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 journal › Article › peer-review

35 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 language	English
Pages (from-to)	11993-11998
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	80
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.5b01922
Publication status	Published - 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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10.1021/acs.joc.5b01922

Cite this

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title = "Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation",

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.",

author = "Seo, {Hong Ahn} and Cho, {Yeon Ho} and Lee, {Ye Sol} and Cheon, {Cheol Hong}",

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: {\textcopyright} 2015 American Chemical Society.",

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doi = "10.1021/acs.joc.5b01922",

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AU - Lee, Ye Sol

AU - Cheon, Cheol Hong

N1 - 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.

PY - 2015/11/18

Y1 - 2015/11/18

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AB - 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.

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

Abstract

Bibliographical note

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