Selective desaturation of amides: a direct approach to enamides

C(sp(3))–H bond desaturation has been an attractive strategy in organic synthesis. Enamides are important structural fragments in pharmaceuticals and versatile synthons in organic synthesis. However, the dehydrogenation of amides usually occurs on the acyl side benefitting from enolate chemistry lik...

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Autores principales: Li, Xinwei, Cheng, Zengrui, Liu, Jianzhong, Zhang, Ziyao, Song, Song, Jiao, Ning
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9365091/
https://www.ncbi.nlm.nih.gov/pubmed/36091215
http://dx.doi.org/10.1039/d2sc02210a
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author Li, Xinwei
Cheng, Zengrui
Liu, Jianzhong
Zhang, Ziyao
Song, Song
Jiao, Ning
author_facet Li, Xinwei
Cheng, Zengrui
Liu, Jianzhong
Zhang, Ziyao
Song, Song
Jiao, Ning
author_sort Li, Xinwei
collection PubMed
description C(sp(3))–H bond desaturation has been an attractive strategy in organic synthesis. Enamides are important structural fragments in pharmaceuticals and versatile synthons in organic synthesis. However, the dehydrogenation of amides usually occurs on the acyl side benefitting from enolate chemistry like the desaturation of ketones and esters. Herein, we demonstrate an Fe-assisted regioselective oxidative desaturation of amides, which provides an efficient approach to enamides and β-halogenated enamides.
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spelling pubmed-93650912022-09-08 Selective desaturation of amides: a direct approach to enamides Li, Xinwei Cheng, Zengrui Liu, Jianzhong Zhang, Ziyao Song, Song Jiao, Ning Chem Sci Chemistry C(sp(3))–H bond desaturation has been an attractive strategy in organic synthesis. Enamides are important structural fragments in pharmaceuticals and versatile synthons in organic synthesis. However, the dehydrogenation of amides usually occurs on the acyl side benefitting from enolate chemistry like the desaturation of ketones and esters. Herein, we demonstrate an Fe-assisted regioselective oxidative desaturation of amides, which provides an efficient approach to enamides and β-halogenated enamides. The Royal Society of Chemistry 2022-07-06 /pmc/articles/PMC9365091/ /pubmed/36091215 http://dx.doi.org/10.1039/d2sc02210a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Li, Xinwei
Cheng, Zengrui
Liu, Jianzhong
Zhang, Ziyao
Song, Song
Jiao, Ning
Selective desaturation of amides: a direct approach to enamides
title Selective desaturation of amides: a direct approach to enamides
title_full Selective desaturation of amides: a direct approach to enamides
title_fullStr Selective desaturation of amides: a direct approach to enamides
title_full_unstemmed Selective desaturation of amides: a direct approach to enamides
title_short Selective desaturation of amides: a direct approach to enamides
title_sort selective desaturation of amides: a direct approach to enamides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9365091/
https://www.ncbi.nlm.nih.gov/pubmed/36091215
http://dx.doi.org/10.1039/d2sc02210a
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AT zhangziyao selectivedesaturationofamidesadirectapproachtoenamides
AT songsong selectivedesaturationofamidesadirectapproachtoenamides
AT jiaoning selectivedesaturationofamidesadirectapproachtoenamides

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