Selective desaturation of amides: a direct approach to enamides

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

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.