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. 2022 Jul 6;13(31):9056-9061.
doi: 10.1039/d2sc02210a. eCollection 2022 Aug 10.

Selective desaturation of amides: a direct approach to enamides

Xinwei Li  1 , Zengrui Cheng  1 , Jianzhong Liu  1 , Ziyao Zhang  1 , Song Song  1 , Ning Jiao  1   2
Affiliations

Selective desaturation of amides: a direct approach to enamides

Xinwei Li et al. Chem Sci. .

Abstract

C(sp3)-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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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Representative drugs containing enamide fragments.
Scheme 1
Scheme 1. The significance and challenges for the synthesis of enamides from amides.
Scheme 2
Scheme 2. Mechanistic studies.
Scheme 3
Scheme 3. Mechanistic investigations.
See this image and copyright information in PMC

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