Recent Advances in Fluoride Ion Activation of Silicon Bonds in Organic Synthesis

Абеле, Э.; Lukevics, É.

doi:10.1515/mgmc.2001.24.6.315

Cited by 23 publications

(9 citation statements)

References 59 publications

(69 reference statements)

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“…Trimethyl(trifluoromethyl)silane, first synthesized in 1984 by Ruppert et al [3] is commonly known as Ruppert's reagent. It is used in the syntheses of perfluorinated compounds and for introducing a trifluoromethyl group by nucleophilic substitution [4][5][6][7]. For these reasons the structural information about (CH 3 ) 3 SiCF 3 are of particular interests and studies by gas phase electron diffraction, microwave spectroscopy and quantumchemical calculations were performed [8].…”

Section: Introductionmentioning

confidence: 99%

High-pressure freezing, crystal structure studies and SiCF3 bond polarizability of trimethyl(trifluoromethyl)silane

Olejniczak

Katrusiak

Vij

2008

Journal of Fluorine Chemistry

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Section: Introductionmentioning

confidence: 99%

High-pressure freezing, crystal structure studies and SiCF3 bond polarizability of trimethyl(trifluoromethyl)silane

Olejniczak

Katrusiak

Vij

2008

Journal of Fluorine Chemistry

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“…The use of inexpensive silanes such as polymethylhydrosiloxane, PMHS, which is a by-product of the silicon industry, or alkoxysilanes, which can be synthesized from inexpensive chlorosilanes [ 21 , 22 , 23 , 24 , 25 , 26 , 27 ], was examined. A variety of catalysts can be used to activate the hydrosilylation: transition metals (especially Ti [ 28 , 29 , 30 , 31 ] and Zn [ 32 , 33 , 34 , 35 , 36 ]) or nucleophiles (especially metal hydroxides / alkoxides [ 37 , 38 , 39 , 40 , 41 ], and fluoride salts [ 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 ]). Because fluoride salts were reported to catalyze ester reductions at room temperature, this mild hydrosilylation / reduction method was investigated for the synthesis of vitamin B 6 .…”

Section: Resultsmentioning

confidence: 99%

Silane Reduction of 5-Hydroxy-6-methyl-pyridine-3,4-dicarboxylic Acid Diethyl Ester: Synthesis of Vitamin B6

Dumond¹,

Gum²

2003

Molecules

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Alternative methods for the synthesis of pyridoxine have been investigated. The key intermediate, 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid diethyl ester (5), was reduced with either a silane monomer (MeSiH(OEt)2) or a polysiloxane (polymethylhydrosiloxane, PMHS) to afford crude pyridoxine. An isolation technique utilizing a commercially available resin was devised, affording the desired product, vitamin B6, in an overall yield of 38-54 % and a purity of 76%.

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“…Recently, a series of fluoride salts were reported for the conversion of aldehyde to corresponding alcohol by PMHS in highly selective and effective environment [56,57]. However, the fluoride salts as homogeneous catalysts are not suitable for economically manufacturing FFA from FUR, for which a novel and recyclable catalyst KF/support is reported in this article.…”

Section: Introductionmentioning

confidence: 98%

Highly Selective Reduction of Bio-Based Furfural to Furfuryl Alcohol Catalyzed by Supported KF with Polymethylhydrosiloxane (PMHS)

et al. 2020

Journal of Chemistry

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Hydrogenation of bio-based furfural (FUR) to furfuryl alcohol (FFA) is tremendously expanding the application of biomass in many industries such as resins, biofuels, and pharmaceuticals. However, mass manufacture of FFA from FUR is restrained by strict requirements of reaction conditions and expensive catalysts. In this work, an economical and benign catalytic system, containing an easily prepared and reusable catalyst 5 wt.% KF/ZrO2 and a low-cost hydrogen source polymethylhydrosiloxane (PMHS), was developed to be efficient for the hydrogenation of FUR to high-value FFA under mild conditions. The catalyst reactivity was found to be remarkably influenced by the support acid-base properties and KF loading doge. In the presence of 5 wt.% KF/ZrO2, a high FFA yield of 97% and FUR conversion of 99% could be obtained at 25°C in just 0.5 h, which was superior to those attained with other tested catalysts. The KF/ZrO2 catalyst could be recycled at least five times, with the FFA yield slightly decreasing from 97% to 71%. The spare decrease in FFA yield is possibly attributed to the catalyst pore blocking, as clarified by SEM, BET, XPS, and ICP-MS measurements of the fresh and reused catalysts.

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Recent Advances in Fluoride Ion Activation of Silicon Bonds in Organic Synthesis

Cited by 23 publications

References 59 publications

High-pressure freezing, crystal structure studies and SiCF3 bond polarizability of trimethyl(trifluoromethyl)silane

High-pressure freezing, crystal structure studies and SiCF3 bond polarizability of trimethyl(trifluoromethyl)silane

Silane Reduction of 5-Hydroxy-6-methyl-pyridine-3,4-dicarboxylic Acid Diethyl Ester: Synthesis of Vitamin B6

Highly Selective Reduction of Bio-Based Furfural to Furfuryl Alcohol Catalyzed by Supported KF with Polymethylhydrosiloxane (PMHS)

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