Effective synthesis of symmetrical oxygen- and nitrogen-heterocycles from electron-deficient alkynes via the catalysis of electrogenerated base and Fe3+ ions

Li, Chuanhua; Yuan, Gaoqing; Zheng, Junhua; He, Zai‐Jun; Qi, Chaorong; Jiang, Huanfeng

doi:10.1016/j.tet.2011.04.058

Cited by 11 publications

(2 citation statements)

References 32 publications

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“…Oxygen-containing heterocyclic molecules occur widely in nature and constitute an important class of compounds because of their diverse biological applications and utility as versatile intermediates in organic synthesis . A recent report revealed that oxygen heterocycles are considered as the second most common type of heterocycle that form part of the structural components in many drugs .…”

Section: Introductionmentioning

confidence: 99%

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO₂: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

et al. 2021

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A method for the synthesis of fused 1,3-dioxolanes was developed by selfcondensation of glyoxal generated in situ by oxidation of acetophenones with SeO 2 in the presence of trifluoroacetic acid. Three molecules of the glyoxal generated by oxidation of ketone with SeO 2 condensed to form architecturally novel oxygencontaining heterocycles (3a-aryldihydro- (phenylmethanones). This reaction provides a unique methodology for the construction of four C−O bonds in a concerted fashion, generating highly embedded oxygen heterocycles from readily available ketones using affordable shelf reagents and simple reaction conditions.

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Section: Introductionmentioning

confidence: 99%

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO₂: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

et al. 2021

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“…Other iron salts, such as iron toluenesulfonate and iron trifluoromethylsulfonate, have also been reported as effective catalysts for the intramolecular hydroalkoxylation of unactivated alkenes, the intermolecular hydroalkoxylation of styrene and the hydrocarboxylation and hydroalkynylation of norbornene . Electrogenerated Fe 3+ with a strong base can catalyze heterocycle formation from electron-deficient alkynes and alcohols . Regioselective double hydrophosphination of arylacetylenes was catalyzed by CpFe(CO) 2 Me .…”

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confidence: 99%

Chemoselective Activities of Fe(III) Catalysts in the Hydrofunctionalization of Allenes

et al. 2012

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A range of tetrahydropyrans and piperidines were produced by Fe(III)-catalyzed intramolecular hydroalkoxylation and hydroamination reactions of allenes. Various Fe catalysts with different counterions were tested. Their activities toward allene and alkene activation depended sensitively on their counterion and reaction conditions. Mechanistic study of the reaction intermediates found a new reaction pattern involving the Fe catalysts and diene substrates.

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Transition Metal‐Catalyzed and Metal‐Free Cyclization Reactions of Alkynes with Nitrogen‐Containing Substrates: Synthesis of Pyrrole Derivatives

Neto

Zeni

2020

ChemCatChem

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This review describes the efforts in the synthesis of pyrrole derivatives using the reaction of alkynes with nitrogen‐compounds under transition metal‐catalyzed and metal‐free conditions, in the past decade. We initially focused on the methods of preparation of pyrrole derivatives using reactions catalyzed by transition metal. In this part, we described the syntheses of 1‐pyrrolines, 2‐pyrrolines, 3‐pyrrolines, pyrroles, and pyrrolidines following an alphabetical order of the transition metal used for the synthesis. Subsequently, we presented the synthesis of these pyrrole derivatives under metal‐free conditions.

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Effective synthesis of symmetrical oxygen- and nitrogen-heterocycles from electron-deficient alkynes via the catalysis of electrogenerated base and Fe3+ ions

Cited by 11 publications

References 32 publications

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO₂: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO₂: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

Chemoselective Activities of Fe(III) Catalysts in the Hydrofunctionalization of Allenes

Transition Metal‐Catalyzed and Metal‐Free Cyclization Reactions of Alkynes with Nitrogen‐Containing Substrates: Synthesis of Pyrrole Derivatives

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Effective synthesis of symmetrical oxygen- and nitrogen-heterocycles from electron-deficient alkynes via the catalysis of electrogenerated base and Fe3+ ions

Cited by 11 publications

References 32 publications

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO2: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO2: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

Chemoselective Activities of Fe(III) Catalysts in the Hydrofunctionalization of Allenes

Transition Metal‐Catalyzed and Metal‐Free Cyclization Reactions of Alkynes with Nitrogen‐Containing Substrates: Synthesis of Pyrrole Derivatives

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Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO₂: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles

Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO₂: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles