Task specific onium salts (TSOSs) as efficient soluble supports for Zard radical addition to olefins

Verron, Julien; Joerger, Jean‐Michel; Pucheault, Mathieu; Vaultier, Michel

doi:10.1016/j.tetlet.2007.04.024

Cited by 14 publications

(4 citation statements)

References 40 publications

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“…Trimethylammonium bis-trifluoromethanesulphonamide [tmba][NTf 2 ] was prepared by following reported procedure. 17 Flash chromatography columns were carried out using MN Kieselgel 60 M gel (40-63 μm, Art. 815381).…”

Section: Methodsmentioning

confidence: 99%

Recyclable hydrotalcite clay catalysed Baylis–Hillman reaction

Srivastava

2013

J Chem Sci

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The Baylis-Hillman reaction using ionic liquid/hydrotalcite clay catalytic system has been observed to be more reactive in terms of yield and reaction rate than DABCO/acetonitrile system. During the process, the reactants enjoy ionic liquid/hydrotalcite clay catalytic system and gives corresponding Baylis-Hillman reaction products in good yield. The application of our catalytic system has been diversifying for the synthesis of lactone ceramide analogue from (S)-Garner aldehyde-methyl acrylate using Baylis-Hillman reaction. Recycling of ionic liquid/hydrotalcite clay catalytic system has also been demonstrated in this report.

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Section: Methodsmentioning

confidence: 99%

Recyclable hydrotalcite clay catalysed Baylis–Hillman reaction

Srivastava

2013

J Chem Sci

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“…'Task-specific onium salts' (TSOSs) are versatile functionalised ionic liquids that can act as soluble supports and they offer considerable potential in radical chemistry. 222 This is highlighted by the use of 314, which reacts with a small excess of alkene (1.3 equiv) and only 0.1 equiv of DLP to give 315 (Scheme 92). Simple hydrolysis gives 316 and the support that can be recycled.…”

Section: Addition Of C-centred Radicals To Non-activated Multiple Bondsmentioning

confidence: 99%

Radicals in organic synthesis. Part 1

Rowlands

2009

Tetrahedron

205

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“…109 In the same year, Vaultier's group also showed that onium salts are efficient soluble ionic supports to carry out intermolecular radical additions of xanthates to olefins (Scheme 61). 110 Radical reactions were usually not successful in solid-phase synthesis because the reaction kinetics differs strongly from those observed under homogenous conditions. The onium ion-supported olefinic radical acceptor 151 or the ion-supported radical precursor 152 can be prepared by simple esterification of the ionic supports.…”

Section: Ion-supported Synthesis Of Small Moleculesmentioning

confidence: 99%

A novel liquid-phase strategy for organic synthesis using organic ions as soluble supports

Huo

Chan

2010

Chem. Soc. Rev.

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This critical review describes a new liquid-phase strategy for organic synthesis by using organic ions as soluble supports. Catalysts or reagents or substrates are immobilized onto organic ions. They are generally soluble in polar organic solvents (e.g. CH(3)CN) or ionic liquids but insoluble in non-polar solvents (e.g. ether or hexanes). Their reactions are carried out in homogeneous solution phase with a polar organic solvent or ionic liquid. After the reaction, the ion-supported species can be phase separated through precipitation from the polar organic solvent by the addition of a less polar organic solvent or extraction with organic solvents from ionic liquids. The ion-supported species can therefore be easily recovered and purified from the reaction mixture by simple washings with the less polar solvent. The ion-tagged species can function in the role of a catalyst, or as a reagent, or as the substrate in the synthesis of small molecules or bio-oligomers. Ion-supported catalysts and reagents can usually be recovered and reused with little diminution of activity. Important biooligomers such as peptides, oligosaccharides and oligonucleotides have been synthesized with this method (136 references).

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Task specific onium salts (TSOSs) as efficient soluble supports for Zard radical addition to olefins

Cited by 14 publications

References 40 publications

Recyclable hydrotalcite clay catalysed Baylis–Hillman reaction

Recyclable hydrotalcite clay catalysed Baylis–Hillman reaction

Radicals in organic synthesis. Part 1

A novel liquid-phase strategy for organic synthesis using organic ions as soluble supports

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