Unusual oxidative free-radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and oxabenzonorbornadiene

Çalışkan, Raşit; Pekel, Tarık; Watson, William H.; Balcı, Metin

doi:10.1016/j.tetlet.2005.07.051

Cited by 37 publications

(6 citation statements)

References 27 publications

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“…To our knowledge, few studies have reported intramolecular cyclopropanation under Mn(OAc) 3 reactivity [42,43,44,45], and only one reported intermolecular reactions between oxabenzonorbornadiene and dimedone [46]. As Mn(OAc) 3 -mediated intermolecular cyclopropanation with trans -stilbene or a similar 1,2-disubstituted alkene has never been reported, the structure of cyclopropane 16 was established by X-ray diffraction analysis (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones

et al. 2013

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A convenient microwave irradiation protocol was utilized for the synthesis of β-ketosulfones 1–5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6–10 were obtained in moderate to good yields starting from 1,1-disubstituted alkenes. Dihydrofurans 11–15 were synthesized in moderate yields and unexpected cyclopropanes 16–19 were obtained in low yields starting from 1,2-disubstituted alkenes. This protocol offers access to various dihydrofurans which could be tested for their antiparasitic potential.

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Section: Resultsmentioning

confidence: 99%

Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones

et al. 2013

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“…[4a,6] In particular, the most employed approach to the construction of substituted 2,3-dihydrofurans is the [3 + 2] annulation, accomplished through many different protocols. Among the traditional methods we can mention the "interrupted" Feist-Bénary reaction, [7] the oxidative coupling reaction between 1,3-dicarbonyl compounds and olefins mediated by stoichiometric manganese(III), [8] cerium (IV), [8d,9a-b] or copper(II), [9c] the 1,3-dipolar reaction involving diazocarbonyl compounds and alkenes cata- lyzed by rhodium(II), [10] ruthenium(II), [11] or copper (II). [12] More recently, some innovative examples of [3 + 2] annulations have been proposed: i) the reaction between ketones and alkenes mediated by copper, [13] palladium, [14] or potassium persulfate, [15] by cooperative systems indium(III)/silver(I) [16] or I 2 /oxidant, [17] or electrochemically promoted; [18] ii) several base-promoted additions to functionalized olefins, [19] alkynyl systems, [20] or carbonyls; [21] iii) Morita-Baylis-Hillman-type annulations; [22] iv) some copper-catalyzed formal cycloadditions involving active methylene compounds and unusual acceptors; [23] v) gold(I)-catalyzed syntheses of silyl-2,3-dihydrofurans.…”

Section: Introductionmentioning

confidence: 99%

Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones

et al. 2021

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A synthetic procedure, catalysed by Ir(ppy)3 under visible‐light irradiation, for the chemodivergent synthesis of 2,3‐dihydrofurans (3) or β,γ‐unsaturated ketones (7) starting from α‐halo ketones (1) and alkenes (2) has been developed. The mild reaction conditions and the redox‐neutral nature of the process make it particularly sustainable avoiding the use of both sacrificial reactants and stoichiometric strong oxidants. Careful experimental investigations, supported by DFT calculations, allowed to disclose in details a possible mechanistic pathway and to direct the synthesis chemodivergently either toward 3 or 7, depending not only on the nature of the substrates, but also on the choice of the experimental conditions.

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“…Among these methods, manganese(III) acetate-catalyzed oxidative free radical addition of 1,3-dicarbonyls to related olefins is one of the most useful [20,[31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis, characterization, and isolation of spiro-benzofuran derivatives are of interest to chemists due to the wide range of biological activity and many methods have been used for their synthesis [27][28][29][30]. Among these methods, manganese(III) acetate-catalyzed oxidative free radical addition of 1,3-dicarbonyls to related olefins is one of the most useful [20,[31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel indanone-based spiro-dihydrobenzofuranderivatives

Gürdere¹,

Dürü²,

Budak³

et al. 2019

Turk J Chem

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In this study, the synthesis and characterization of novel indanone-based spiro-dihydrobenzofuran derivatives were examined. Firstly, chalcone-like compounds 4a-k, (E)-2-benzylidene-2,3-dihydro-1 H-inden-1-one derivatives, were synthesized by the base-catalyzed addition of benzaldehyde derivatives to 2,3-dihydro-1 H-inden-1-one. Then Mn(OAc) 3-mediated addition of dimedone (2) to the chalcone-like compounds gave two novel spiro-dihydrobenzofuran isomers: (3 S)-6,6-dimethyl-3-aryl-6,7-dihydro-3 H-spiro [benzofuran-2,2'-indene]-1',4(3' H ,5 H)-dione (5a-k) and (2' S)-6,6-dimethyl-2-aryl-6,7-dihydro-2 H-spiro[benzofuran-3,2'-indene]-1',4(3' H ,5 H)-dione (6a-k) in good yields. The isomers were separated by column chromatography and their structures were elucidated on the basis of spectral data (NMR, IR) and elemental analysis.

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Unusual oxidative free-radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and oxabenzonorbornadiene

Cited by 37 publications

References 27 publications

Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones

Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones

Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones

Synthesis and characterization of novel indanone-based spiro-dihydrobenzofuranderivatives

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