Ambient and aerobic carbon–carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

Yu, Qing; Zhang, Yating; Wan, Jie‐Ping

doi:10.1039/c9gc01357a

Cited by 103 publications

(43 citation statements)

References 85 publications

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“…[94][95][96][97][98][99][100][101][102][103][104][105] Particularly, visible-light photoredox catalysis is an ideal tool to initiate radical cascade reactions for the synthesis of heterocycles. [106][107][108][109][110][111][112][113][114][115][116][117][118] In 2017, Hong's group reported a visible-light-enabled radical strategy to synthesize spiroepoxy chroman-4-one derivatives 74 via a tandem oxidation/radical cyclization/epoxidation process (Scheme 14). [119] The optimal conditions involving the use of Ru(bpy) 3 Cl 2 ·6H 2 O, TBHP, and K 2 CO 3 in iPrOAc at room temperature with irradiation of blue LEDs demonstrated broad substrate scope and good functional group tolerance with respect to both 2-(allyloxy)arylaldehydes 72 and (2-(allyloxy)aryl)methanols 73.…”

Section: Visible-light-promoted Reactionsmentioning

confidence: 99%

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

Xiong

Wei

et al. 2020

Eur J Org Chem

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Radical cascade cyclizations of o‐allyloxybenzaldehydes have emerged as a powerful strategy for the synthesis of 3‐substituted chroman‐4‐ones. This minireview summarizes the incorporation of various functional groups into the C3‐position of chroman‐4‐ones by employing appropriate radical precursors through transition‐metal‐free systems, silver‐catalyzed systems, or visible‐light‐promoted systems.

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Section: Visible-light-promoted Reactionsmentioning

confidence: 99%

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

Xiong

Wei

et al. 2020

Eur J Org Chem

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“…When o-phenylenediamine was employed in the reaction system, quinoxalin-2(1H)ones were obtained with both satisfactory yields and substrate tolerance (Scheme 15). 19 In this reaction, molecular oxygen is activated to form singlet oxygen 1 O 2 under visible-light irradiation, which then couples to the C=C double bond of the enaminone to give 1,2-dioxetane 17. Subsequently, ring opening of 17 and formation of a new N-O bond produces 18, which is then attacked by the alcohol to form the zwitterion intermediate 19.…”

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

confidence: 99%

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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“…On the basis of these results mentioned above and literature, two possible reaction pathways are proposed in Scheme . In pathway a: hemiketalization of ketone 1 in the presence of sulfuric acid and alcohol delivers intermediate A , which further undergoes dehydration to afford vinyl ether B .…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

Metal‐Free, Visible‐Light‐Induced Selective C−C Bond Cleavage of Cycloalkanones with Molecular Oxygen

Hong

Duan

Liu

et al. 2020

Chemistry A European J

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A metal‐free, visible‐light‐induced oxidative C−C bond cleavage of cycloketones with molecular oxygen is described. Cooperative Brønsted‐acid catalysis and photocatalysis enabled selective C−C bond cleavage of cycloketones to generate an array of γ‐, δ‐ and ϵ‐keto esters under very mild conditions. Mechanistic studies indicate that singlet molecular oxygen (1O2) is responsible for this transformation.

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Ambient and aerobic carbon–carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

Abstract: With a low loading of Rose Bengal (1 mol%) and green LED irradiation, α-ketoesters are efficiently synthesized with excellent product diversity and selectivity via the ambient cleavage of the enaminone CC double bond.

Cited by 103 publications

References 85 publications

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

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

Metal‐Free, Visible‐Light‐Induced Selective C−C Bond Cleavage of Cycloalkanones with Molecular Oxygen

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