Metal‐Free C=C Double Bond Cleavage on Enaminones for the Synthesis of α‐Ketoamides by Free‐Radical Aerobic Oxygenation

Yang, Yiming; Zhong, Guofeng; Fan, Junfen; Liu, Yunyun

doi:10.1002/ejoc.201900660

Cited by 18 publications

(3 citation statements)

References 76 publications

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“…Based on this work, Liu and co-workers recently developed a metal-free strategy to achieve this reaction by combining BPO and NIS promotion for the synthesis of -keto amides (Scheme 13). 17 Unlike the newly formed carbonyl oxygen reported above being derived from water, in this reaction, it should be derived from oxygen, and this was confirmed by 18 O-labeling experiments. A series of single-electron transfers (SET) of the enaminones by BPO and NIS generates intermediates 9, which are then converted into the 1,2-dioxetane 10 via an intramolecular free-radical addition.…”

Section: Synthesis Of -Ketoamides -Ketoesters and 12-diketonessupporting

confidence: 63%

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Huang

2020

Synthesis

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Enaminones are gaining increasing interest because of their unique properties and their importance in organic synthesis as versatile building blocks. N,N-Dimethyl enaminones offer a better leaving group (a dimethylamine group) than other enaminones, and allow further elaboration via a range of facile chemical transformations. Over the past five years, there have been an increasing number of reports describing the synthetic applications of N,N-dimethyl enaminones. This review provides a comprehensive overview on the synthetic applications of N,N-dimethyl enaminones that have been reported since 2016.1 Introduction2 Direct C(sp2)–H α-Functionalization2.1 Synthesis of α-Sulfenylated N,N-Dimethyl Enaminones2.2 Synthesis of α-Thiocyanated N,N-Dimethyl Enaminones2.3 Synthesis of α-Acyloxylated N,N-Dimethyl Enaminones3 Functionalization Reactions via C=C Double Bond Cleavage3.1 Synthesis of Functionalized Methyl Ketones3.2 Synthesis of α-Ketoamides, α-Ketoesters and 1,2-Diketones3.3 Synthesis of N-Sulfonyl Amidines4 Construction of All-Carbon Aromatic Scaffolds4.1 Synthesis of Benzaldehydes4.2 Synthesis of the Naphthalenes5 Construction of Heterocyclic Scaffolds5.1 Synthesis of Five-Membered Heterocycles5.2 Synthesis of Six-Membered Heterocycles5.3 Synthesis of Quinolines 5.4 Synthesis of Functionalized Chromones5.5 Synthesis of Other Fused Polycyclic Heterocycles6 Conclusions and Perspectives

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Section: Synthesis Of -Ketoamides -Ketoesters and 12-diketonessupporting

confidence: 63%

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Huang

2020

Synthesis

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“…Previously, the synthesis of α-ketoamides was developed from various substrates, and α-ketoacids (Scheme a) are one of the most important among these. Other approaches used α-hydroxyamides, α-aminoamides, acetophenone, aryl halides, α-ketoaldehydes, styrenes, phenylacetylenes, enaminone, vinylazides, diazo compounds, etc. It is worth mentioning that these methods were executed using metal catalysts, oxidants, and other reagents under different conditions.…”

Section: Introductionmentioning

confidence: 99%

Visible-Light-Promoted Metal- and Photocatalyst-Free Reactions between Arylglyoxylic Acids and Tetraalkylthiuram Disulfides: Synthesis of α-Ketoamides

Sarkar,

Pal,

Mukherjee

et al. 2024

J. Org. Chem.

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A convenient and new synthetic approach has been developed for the oxidative cross-coupling of the C−N bond through the reaction between arylglyoxylic acids and tetraalkylthiuram disulfides. The reaction proceeds under ambient air at room temperature in the presence of visible light. This reaction offers a metal-, base-, photocatalyst-, and solvent-free synthesis of various α-ketoamides with moderate to excellent yields via the radical pathway. In addition, this protocol demonstrates the potential application of a gram-scale synthesis.

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“…Practically, the amidation of α-oxocarboxylic acids has turned out to be a general approach for obtaining α-ketoamide and its derivatives. Besides, other substrates such as acetophenones, α-ketoaldehydes or keto acids, arylethanols, styrenes, phenylacetylenes, alkylarenes, halides, α-hydroxyketone, 9 arylacetic acid, 10 enaminone, 11 benzoylacetonitrile, 12 α-aminocarbonyl, 13 diazo compounds, 14 benzofuran-3(2 H )-ones, 15 etc. have been introduced to synthesize α-ketoamides (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%