Amberlyst-15 as a new and reusable catalyst for regioselective ring-opening reactions of epoxides to β-alkoxy alcohols

Liu, Yuheng; Liu, Qiu‐Shuang; Zhang, Zhan‐Hui

doi:10.1016/j.molcata.2008.09.003

Cited by 90 publications

(14 citation statements)

References 44 publications

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“…The synthetic route for such compounds commonly proceeds via ring-opening of oxiranes (epoxides) using traditional Lewis acids such as Cu(BF 4 ) 2 [2,21], Sn(OTf) 2 [11], BF 3 [22], Sc(OTf) 3 [24], and traditional solid acids such as amberlyst-15 [10]. Modified Lewis acid complexes based on salen [5,12] and porphyrin [23] ligands have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Ring-Opening of Oxiranes using Taeniolite-Supported Tris(β-Diketonato)Zirconium

2012

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Abstract.A series of tris(β-diketonato)zirconium(IV) complexes was immobilized into a synthetic clay structure of Taeniolite by an ion-exchange method to generate organic/inorganic hybrid compounds. The hybrid compound served as a good catalyst for ring-opening reactions of methyl, ethyl, and dimethyl oxiranes with various alcohols to generate primary alkoxy alcohols in appreciable selectivity. This method describes a technique to immobilize cationic zirconium complexes without losing selectivity.

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Section: Introductionmentioning

confidence: 99%

Ring-Opening of Oxiranes using Taeniolite-Supported Tris(β-Diketonato)Zirconium

2012

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“…In this regard Amberlyst 15 possesses properties such as non-hazardous, chemical and physical stability and can be recycled and used over a prolonged period. It catalyzes a wide variety of reactions in heterogeneous phase [24][25][26][27][28][29][30][31][32][33][34][35][36], and recently was used for the synthesis of bis (heterocyclyl) methane derivatives from heteroaryl species and carbonyl substrates [37].…”

Section: Resultsmentioning

confidence: 99%

New Green Synthesis and Antineoplastic Activity of Bis (3-Arylimidazolidinyl-1) Methanes

Perillo¹,

Villalonga²,

Amiano³

et al. 2013

OJMC

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A new green synthesis and anti-tumor activity of the series of bis (3-arylimidazolidinyl-1) methanes 1 -6 are described. The compounds were synthesized from the corresponding N-arylethylenediamine and trioxane as sources of formaldehyde and the reactions were performed in heterogeneous phase catalyzed by an acidic ion-exchange resin (Amberlyst 15). The compounds were tested with the Sulforhodamine B assay according to the protocol of the National Cancer Institute for several cell lines. The results were expressed as percentage inhibition of growth cell in comparison with the full growth of the cells without treatment. Cytotoxicity on normal cells using the Annexing-PI staining and flow cytometry has been evaluated. The parent compound, bis(3-phenylimidazolidinyl-1)methane 1 and the monohalogenated derivatives 4-chlorophenyl 3 and 3-bromophenyl 5 showed antineoplastic activity, 60%, 82% and 89% inhibition growth cell respectively on the human colon cell line (HCT116). The 4-tolyl derivative 6 presented inhibitory activity (73% inhibition of growth cell) on human lung adenocarcinoma cell line (A549) and 62% on human mammary cell line MCF-7.

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“…A continuous-flow apparatus for the hydrolytic kinetic resolution of terminal epoxides over silicabound Co(Salen)-complex catalyst was previously described by Annis and Jacobsen [16]. Various recyclable solid catalysts, including, amberlyst resin [17], sulfonic acid-functionalized SBA-15 [18] and polymer [16] have been investigated in the literature. In our setup the acidic silica was finely mixed with inert fuller's earth (1:4 w/w) then the column was carefully packed.…”

Section: Resultsmentioning

confidence: 99%