Transition Metal-Free Oxidative Cross-Coupling Reaction of Activated Olefins with N-Alkyl Amides

Abstract

The K2S2O8-mediated transition metal-free oxidative cross-coupling reaction of activated olefins with N-alkyl amides was developed, and the reaction gave N-allylic amides in moderate to good yield. This reaction protocol was suitable for different kinds of activated olefins.

A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

“…The CuO-catalyzed reaction of cinnamic acids with DMAc and di-tert-butyl peroxide led to decarboxylative alkenylation giving the corresponding N-cinnamyl-N-methylacetamides (Scheme 39(a1)) while 3-methylbut-2-enoic acid afforded (N-methylacetamido)methyl 3-methylbut-2-enoate (Scheme 39(a2)) [126]. Cross-coupling with the elimination of the sulfonyl or nitro group was also observed from the reaction of vinylsulfones, ((phenylethynyl)sulfonyl)benzene and β-nitrostyrenes using DM in the presence of either a diaryl ketone under visible-light irradiation (Scheme 39b) [128] or a peroxydisulfate (Scheme 39c) [129]. The CuO-catalyzed reaction of cinnamic acids with DMAc and di-tert-butyl peroxide led to decarboxylative alkenylation giving the corresponding N-cinnamyl-N-methylace tamides (Scheme 39(a 1 )) while 3-methylbut-2-enoic acid afforded (N-methylacetamido) methyl 3-methylbut-2-enoate (Scheme 39(a 2 )) [126].…”

“…The CuO-catalyzed reaction of cinnamic acids with DMAc and di-tert-butyl peroxide led to decarboxylative alkenylation giving the corresponding N-cinnamyl-N-methylacetamides (Scheme 39(a1)) while 3-methylbut-2-enoic acid afforded (N-methylacetamido)methyl 3-methylbut-2-enoate (Scheme 39(a2)) [126]. Cross-coupling with the elimination of the sulfonyl or nitro group was also observed from the reaction of vinylsulfones, ((phenylethynyl)sulfonyl)benzene and β-nitrostyrenes using DM in the presence of either a diaryl ketone under visible-light irradiation (Scheme 39b) [128] or a peroxydisulfate (Scheme 39c) [129].…”

Mechanochemical-assisted decarboxylative sulfonylation of α,β-unsaturated carboxylic acids with sodium sulfinate salts

“…Compound 3 was subjected to a reaction with pyrrolidin-2-one in DMA at 110 °C with (NH 4 ) 2 S 2 O 8 as an oxidant under air, resulting in the required product 56 in 74% yield (Scheme 4). 13…”

Nitroxide‐Catalyzed Oxidative Amidation of Aldehydes to Yield N‐Acyl Azoles Using Sodium Persulfate

“…Persulfate salts are inexpensive, widely available crystalline solids that are very soluble in water and reasonably soluble in aqueous acetonitrile, small chain alcohols, and acetone and are beginning to attract interest in organic synthesis [34–38] . The peroxydisulfate ion (S 2 O 8 2− ) is a strong oxidant with an estimated standard redox potential of 2.01 V, this being higher than that of other peroxygen‐containing compounds such as hydrogen peroxide or sodium bisulfite.…”