Polymer-supported chloroaluminate catalysts for the Diels–Alder reaction of cyclopentadiene with methyl methacrylate

Bae, Hyun Woo; Han, Jinyu; Jung, Srun; Cheong, Minserk; Kim, Hoon Sik; Lee, Je Seung

doi:10.1016/j.apcata.2007.07.023

Cited by 19 publications

(11 citation statements)

References 23 publications

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“…특히 IL은 유기 양이온과 무기 음이온의 구조를 변화시킴으로 서 물리화학적 특성을 조절할 수 있고, 유기 화합물의 반응에 촉매로 적용 할 때, 분리가 용이하여 재활용할 수 있다는 장점을 가진다 [12]. 이러한 배 경에서 IL은 alkylation [13,14], dimerization [15,16], Diels-Alder reaction [17], Friedel-Crafts reaction [12] 등에서 적용 연구가 보고되고 있다. …”

Section: 서 론 1)unclassified

A Study on the Reaction Pathway for Isomerization of Tetrahydrotricyclopentadiene Using Ionic Liquid Catalyst

Kim

Han²,

Jeon³

et al. 2015

Applied Chemistry for Engineering

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The kinetic behavior of tetrahydrotricyclopentadiene (THTCPD) isomerization was studied by using two kinds of chloroaluminate ionic liquid (IL) catalyst with different Lewis acidity. THTCPD isomerization pathway was discussed under the different temperature and time as reaction parameters using IL catalysts consisting of 1-butyl-3-methylimidazolun chloride (BMIC)/AlCl3 with low acidity and pyridine hydrochloride (PHC)/AlCl3 with high acidity. The conversion of THTCPD isomerization increased with increasing Lewis acidity of IL catalyst. The THTCPD isomerization pathway changed as a function of reaction temperature and catalyst acidity. In the case of BMIC/AlCl3 IL catalyst, THTCPD isomerization pathway was similar to that of using conventional AlCl3 catalyst. However, two different types of additional pathways (endo, exo, endo-NB → exo, exo, endo-NB → exo, exo, exo-NB and endo, exo, endo-NB → exo, exo, endo-NB → exo, exo, exo-CP) were appeared when using PHC/AlCl3 IL catalyst.

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Section: 서 론 1)unclassified

A Study on the Reaction Pathway for Isomerization of Tetrahydrotricyclopentadiene Using Ionic Liquid Catalyst

Kim

Han²,

Jeon³

et al. 2015

Applied Chemistry for Engineering

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“…Polymers with chirality incorporated into the backbone have been widely studied as catalyst supports for a range of asymmetric C-C bond forming reactions including Diels-Alder cycloadditions, oxidations and hydrogenations. [4][5][6][7][8] In contrast, the concept of immobilising an ionic liquid in the form of a cation-decorated polymer, e.g. in the form of a polyelectrolyte, to combine the favourable properties of ionic liquids with the advantages of heterogenisation as well as overcome leaching and improve long term stability in asymmetric catalysis has been far less studied.…”

Section: Introductionmentioning

confidence: 99%

An efficient Cu(ii)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation

et al. 2014

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The asymmetric Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methylpyruvate and 1-phenyl-1-trimethylsilyloxyethene have been catalysed by heterogeneous copper(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase (PIILP) systems generated from a range of linear and cross linked ionic polymers. In both reactions selectivity and ee were strongly influenced by the choice of polymer. A comparison of the performance of a range of Cu(II)-bis(oxazoline)-PIILP catalyst systems against analogous supported ionic liquid phase (SILP) heterogeneous catalysts as well as their homogeneous counterparts has been undertaken and their relative merits evaluated. Scheme 1 Asymmetric Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene catalysed by 10 mol% Cu(II)-bis(oxazoline) complexes. † Electronic supplementary information (ESI) available: 1 H NMR, 13 C NMR and 19 F NMR spectra for the polymer precursors synthesised. TGA, SEM and FTIR traces for the polymers used. HPLC traces of exo and endo-cycloadducts and aldol adducts formed. See

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“…The acidity of the resulting IL can be controlled by varying the relative amounts of AlCl 3 and organic chloride. Although there are several reports on the immobilization of ILs on solid supports, [4][5][6][7][8][9][10][11][12][13] to the best of our knowledge, few examples are known for immobilized chloroaluminate ILs. A melt having an AlCl 3 mole fraction of exactly 0.5, where AlCl 4is the only anion present, is referred to as a neutral melt.…”

Section: Introductionmentioning

confidence: 99%

“…Chloroaluminate melts are designated as basic when the AlCl 3 mole fraction is smaller than 0.5 and the melts contain Cland AlCl 4 -, a Lewis bases. 9,12 The benzimidazole and its derivatives constitute a very important, privileged class of nitrogen-containing heterocyclic compounds that show various biological activities, such as anticonvulsant, 14 antidepressant, 15 antihistamine, 16 anti-ulcer, 17 antihypertensive, 18 anticancer, 19 anti-inflammatory, 20 anthelmintic, 21 antiprotozoal 22 and antitumour properties. Finally, an acidic chloroaluminate melt is one in which the AlCl 3 mole fraction is larger than 0.5.…”

Section: Introductionmentioning

confidence: 99%

Polystyrene-supported pyridinium chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for selective synthesis of benzimidazoles

Boroujeni¹,

Zhianinasab²,

Jafarinasab³

2013

JSCS

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Polystyrene-supported pyridinium chloroaluminate ionic liquid was prepared from the reaction of Merrifield resin with pyridine followed by reaction with aluminium chloride. This catalyst was used as a new chemoselective Lewis acid catalyst for the exclusive synthesis of 2-substituted benzimidazoles from the reaction of aldehydes with o-phenylenediamines. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency

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Polymer-supported chloroaluminate catalysts for the Diels–Alder reaction of cyclopentadiene with methyl methacrylate

Cited by 19 publications

References 23 publications

A Study on the Reaction Pathway for Isomerization of Tetrahydrotricyclopentadiene Using Ionic Liquid Catalyst

A Study on the Reaction Pathway for Isomerization of Tetrahydrotricyclopentadiene Using Ionic Liquid Catalyst

An efficient Cu(ii)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation

Polystyrene-supported pyridinium chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for selective synthesis of benzimidazoles

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