Fluorous Biphase Chemistry

Horváth, István T.

doi:10.1021/ar970342i

Cited by 754 publications

(328 citation statements)

References 62 publications

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“…The present work will show that the CO 2 pressure can increase the solubility of the fluorinated catalysts in the neat organic substrate phase, promoting the rate of Heck reaction and the depressurization can cause the catalysts to precipitate from the liquid mixture, allowing them to be recycled. That is, the transformable heterogeneous and homogeneous catalysis can be achieved with the fluorinated catalysts and CO 2 without using additional organic and fluorous solvents, which are both needed for fluorous biphasic catalytic reactions [34][35][36]. The potential of the present CO 2 pressure tunable heterogeneous/homogeneous catalytic reaction system has also been studied for Sonogashira reaction [11,37,38] of iodobenzene and phenylacetylene under similar conditions.…”

Section: Methodsmentioning

confidence: 93%

Carbon dioxide pressure induced heterogeneous and homogeneous Heck and Sonogashira coupling reactions using fluorinated palladium complex catalysts

Akiyama

Meng

Fujita

et al. 2009

The Journal of Supercritical Fluids

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The Heck reaction of iodobenzene and methyl acrylate was investigated with CO 2 -philic Pd complex catalysts having fluorous ponytails and the organic base triethylamine (Et 3 N) in the presence of CO 2 under solventless conditions at 80 C. The catalysts are not soluble in the organic phase in the absence of CO 2 and the reaction occurs in a solid-liquid biphasic system. When the organic liquid mixture is pressurized by CO 2 , CO 2 is dissolved into the organic phase and this promotes the dissolution of the Pd complex catalysts. As a result, the Heck reaction occurs homogeneously in the organic phase, which enhances the rate of reaction. This positive effect of CO 2 pressurization competes with the negative effect that the reacting species are diluted by an increasing amount of CO 2 molecules dissolved. Thus, the maximum conversion appears at a CO 2 pressure of around 4 MPa under the present reaction conditions. The catalysts are separated in the solid granules by depressurization and are recyclable without loss of activity after washing with n-hexane and/or water. When the washing is made with hexane alone, the catalytic activity tends to increase on the repeated Heck reactions, probably due to the accumulation of such a base adduct as Et 3 NHI on the catalysts. When the washing is further made with water, however, the base adduct is taken off from the catalysts and they show similar activity levels in the repeated runs. The potential of CO 2 pressure tunable heterogeneous/homogeneous reaction system has also been investigated for Sonogashira reactions of iodobenzene and phenylacetylene under similar conditions.

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Section: Methodsmentioning

confidence: 93%

Carbon dioxide pressure induced heterogeneous and homogeneous Heck and Sonogashira coupling reactions using fluorinated palladium complex catalysts

Akiyama

Meng

Fujita

et al. 2009

The Journal of Supercritical Fluids

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“…近年来, 寻找可替代的绿色溶剂是绿色有机合成努力的方向之一. 目前, 可替代的新型反应介质主要包括水 [12] 、超临界流体 [13] 、全氟烃 [14] 、液态聚乙二醇 [15] 和离子液体 [16] 等. 离子液体作为新兴的绿色化学溶剂, 反应可在均相催化反应体系中进行, 对水和空气稳定, 便于反应操作和处理, 易回收, 有望解决化学反应过程中出现的污染问题 [17] .…”

Section: 另外绿色化学(或环境友好化学)已经引起化学家unclassified

Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturatedγ-Lactones in Ionic Liquids

李建晓¹,

李春生²,

杨少容³

et al. 2015

Chin. J. Org. Chem.

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“…Horvath and Rabai investigated a fluorous biphasic system, which offers great integration of a homogeneous reaction and subsequent separation using a fluorous tag. 27,28 Perfluorocarbons can dissolve only fluoroustagged (highly fluorinated) compounds, and are immiscible with non-fluorinated organic solvents at ambient temperature. Thus, the application of fluorous compounds for extraction is widely spread.…”

Section: Introductionmentioning

confidence: 99%

A Fluorous Biphasic Solvent Extraction System for Lanthanides with a Fluorophilic β-Diketone Type Extractant

et al. 2015

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The properties of a fluorous solvent extraction system for trivalent lanthanide metal ions are reported. A fluorinated extractant, 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-(2-thienyl)-1,3-nonanedione, and HFE-7200 (C4F9OC2H5) as the extraction solvent were chosen. With this fluorous extractant/solvent combination, higher extraction ratios and separation factors compared to a conventional organic solvent system (thenoyltrifluoroacetone in CHCl3) were achieved for 5 heavy lanthanide ions (Lu, Yb, Tm, Er and Ho). On the other hand, light lanthanide ions (Nd, Pr, Ce and La) are hardly extracted, therefore enabling the mutual separation of light lanthanides from middle or heavy lanthanide ions.

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Fluorous Biphase Chemistry

Cited by 754 publications

References 62 publications

Carbon dioxide pressure induced heterogeneous and homogeneous Heck and Sonogashira coupling reactions using fluorinated palladium complex catalysts

Carbon dioxide pressure induced heterogeneous and homogeneous Heck and Sonogashira coupling reactions using fluorinated palladium complex catalysts

Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturatedγ-Lactones in Ionic Liquids

A Fluorous Biphasic Solvent Extraction System for Lanthanides with a Fluorophilic β-Diketone Type Extractant

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