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...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2022-08, Vol.13 (31), p.956-961
Main Authors: Li, Xinwei, Cheng, Zengrui, Liu, Jianzhong, Zhang, Ziyao, Song, Song, Jiao, Ning
Format: Article
Language:English
Subjects:
Amides
Chemistry
Dehydrogenation
Desaturation
Esters
Hydrogen bonds
Ketones
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 -halogenated enamides. A novel and regioselective N -,β-desaturation and dehydrogenative N -β-halogenation of amides was developed. This chemistry with high selectivity and broad substrate scope provides an efficient approach to enamides from simple amides.
ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc02210a